


A Thousand Lies

by goldenraeofsun



Category: Supernatural
Genre: Accountant Castiel (Supernatural), Alternate Universe - Criminals, Alternate Universe - Human, Angst with a Happy Ending, Bisexual Dean Winchester, Con Artist Dean Winchester, Dean Winchester Has Self-Worth Issues, Dubcon Kissing, M/M, Mutual Pining, Non-Consensual Drug Use, Pansexual Castiel (Supernatural), Past Dean Winchester/Other(s), Unrequited Crowley (Supernatural)/Dean Winchester, not cas/dean
Language: English
Status: Completed
Published: 2020-07-14
Updated: 2020-08-03
Packaged: 2021-03-04 23:33:58
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 10
Words: 72,610
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25264675
Author URL: https://archiveofourown.org/users/goldenraeofsun/pseuds/goldenraeofsun
Summary: Dean Winchester is the best con artist in the continental US. Conscripted into the life after a stupid mistake as a teenager, he works for a man only known as the Lightbringer. He specializes in the marriage con, tricking his marks into falling in love with him and bolting after the honeymoon with everything they own.But the morning before his meticulously planned meet-cute with his newest assignment, he runs into an adorably clueless accountant named Cas in a coffee shop, and Dean’s entire view on life implodes.
Relationships: Castiel/Dean Winchester
Comments: 269
Kudos: 323
Collections: The Destiel Fan Survey Favs Collection





	1. Prologue: The End

**Author's Note:**

> Thank you so much, [mac](https://archiveofourown.org/users/a_qualitystudentharmony) and [Touch](https://archiveofourown.org/users/BrewedMayhem) for the beta reads!
> 
> Lastly and most importantly, a tremendous thank you to [tiamatv](https://archiveofourown.org/users/tiamatv/) who leaves such lovely comments when beta-ing, and is always game to talk through my half-formed ideas ♥
> 
> This story is complete. Chapters will be posted every 2-3 days.

Cole almost doesn’t hear his phone chime with a new text as he sprints through his house, looking for his husband. Terrifying scenarios flit through Cole’s head. Kidnapped for ransom. Held up at gunpoint. Maybe even _dead._

He stops in their bedroom. The covers are still thrown back from when they’d gone to work in the morning. He checks his phone.

With trembling hands he reads the text: a link to a website. He clicks it.

His husband’s face appears on the screen, thankfully not beaten black-and-blue.

It had started like a normal day. Waking up in his husband’s arms. Making breakfast together. Carpooling to work. At lunch, everything went off the rails.

The deli where he got his sandwich declined all his credit cards.

His bank emailed later in the afternoon. Suspiciously large withdrawals. A visit to his safety deposit box.

Cole jumped in his car and sped back home – work would have to wait.

Staring at his phone, Cole doesn’t even hear the first few words out of his husband’s mouth, too relieved to see the familiar sandy-blond hair and darker beard, bright green eyes hidden behind black, thick-rimmed glasses. He restarts the video.

“Hey, Cee, I know you must be very confused. The checking account, the cash, the credit cards… it’s a shock,” he says, his tone even and understanding.

Cole’s heart stops dead in his chest.

“There’s no easy way to say it: you’ll never see me again. The sooner you accept it, the better off you’ll be. Over the next few days, I’m sure you’ll ask yourself what you could have done differently, what was real and what was not. Don’t dwell on the past, babe.”

Cole can barely hear past the roaring in his ears – or are they filled with cotton, muffling everything except the riot going on in his head? The phone nearly slips out of his weak grasp as Cole sags against the nearest wall. He slides down with a thump to sit on the floor by the foot of their bed.

“Don’t try to find me,” his husband is saying. “Go to the bed, look under my pillow.”

Cole crawls to the bed on his knees and reaches up with one hand to blindly hunt around. He pulls out a folder and drops the phone on the floor to rifle through it.

“Listen to me very carefully. If you ever go to the police, everyone in your family, everyone in the world, will know. Don’t put your mother through that,” his husband says. “If she knew what was in there… Just don’t. It’s best to just leave it be. Leave me be.”

Cole’s hands shake as he reads over the real military records of his discharge – the records that Cole had paid for in blood, sweat, and tears to keep hidden forever. Had his husband known about this the whole time?

“Okay, now the hard part,” his husband sighs, running a hand across his chin like he always does when he’s thinking deeply, “You will find love again. I know it. Goodbye, Cole.”

Cole calls the number back, waiting with bated breath for barely a half second before an automated voice informs him that the line has been disconnected. He calls back and gets the same message. He calls again.

Cole slumps back against the bed. Time passes in a desperate, angry haze.

He only rouses himself as his phone rings, and Cole flinches as he sees his mother’s face appear on the screen. “Hey, Mom,” he says hoarsely as he answers the call.

“Are you alright?” his mom asks at once. “I hoped to catch you at lunch. Did you eat something funny? You sound off.”

Cole licks his lips, glances at the papers strewn across his bedroom floor. “It’s Mal – my husband.” He breaks off, muffling an emotional gasp with his fist.

“I know who he is,” his mother says, amused, as Cole tries to regain control of himself.

“Malcolm’s gone.”


	2. The Approach

**Summary for the Chapter:**

> Dean gets in line behind the only person waiting in front of the bar, a man in a boxy suit squinting at the menu board above baristas’ heads like it’s the Rosetta Stone. Dean waits for second, his usual morning exhaustion warring with impatience for caffeine. “Hey,” he says, tapping the guy once on the shoulder. “You want to wake up or actually enjoy it?”
> 
> The guy turns around.
> 
> Christ, that’s some blue in those eyes. 
> 
> The guy blinks a couple of times, a hint of panic in his startled expression. He stares at Dean.

Dean rubs the bridge of his nose, immeasurably thankful to be rid of the stupid glasses. Of all the things he hated about Malcolm – the pastel shirts and pressed khakis, the hipster beard, the uncomfortable shoes that pinched no matter how hard he tried to wear them in – the glasses were the worst. But he needed to impress Mama Trenton and make Cole fall in love with him, so he paid his dues to the J Crew mothership.

He turns off at the next exit, a pit stop on the Jersey turnpike, and scans the parking lot for the Impala. It’s been too long since he’s been inside his baby, and he nearly cries as he sees her near the back. She’s parked a little too close to a grey Volvo on her left, but she looks to be in once piece.

He parks on her right and barely has his two feet on the pavement before Jo rushes him, wrapping her arms around his torso and squeezing tight. 

“Woah, hey!” Dean exclaims.

She steps back, beaming up at him. “Hey, yourself,” she says, punching him on the shoulder. “You didn’t say how the blow off went.”

“It’s nice to see you too, kid, even though I saw you _three days ago,_ ” Dean says as he slings an arm around her shoulder. “And it went fine. He's gonna keep quiet, just like they always do. Where’s Charlie?”

“Reviewing the next assignment for the debrief.”

“Nerd.”

“That’s what I told her.”

Dean waves as they come into view, and Charlie springs up from the table to hug him hello. 

“Who’s the next mark?” Dean asks as they break apart and Charlie hands out copies of the main intel.

“Fergus MacLeod,” she says as he raises his laptop screen. “Goes by Crowley. He’s a senior partner of Daimonion, the largest financial consultancy firm in the Los Angeles area.”

Dean punches his fist in the air. “Looks like you’re on deck, Jo,” he says with a grin as Jo scowls. Dean whistles at the picture, taken at some corporate event. “Good luck with that one.”

Jo scans her papers and snorts. “Way to jump the gun, Dean,” she says, pointing at a spot on the profile. “Says here he’s into ruggedly handsome _guys.”_

Dean groans. “Come on! I just worked my ass off for Trenton. Now I have to do it all again?” 

Charlie reaches over to pat Dean on the arm. “The Lightbringer bumped Crowley up the pecking order. Rush job. Needs to be taken ASAP.”

Dean runs a hand through his hair, frowning heavily. “Great. Just fucking perfect.”

Charlie spares him one more sympathetic look. “Here are your new identities.” She hands out the personal files.

“What the hell?” Dean gapes as he scans his new social security card, driver’s license, and passport. “Michael Smith? Could I get a more boring name?”

“Says the guy who liked _Malcolm_ and _Kurt._ You have terrible taste in names,” Jo snickers. “It says here his dog walker quit last week. Maybe that’s my play?”

“Will that give you enough access to his place?” Dean asks.

Jo frowns. “It says here he needs Juliet and Ramsay walked twice a day – three times when he’s working late.”

“Great,” Dean says as he holds out his hand. “You don’t need my baby then. Keys.”

Jo rolls her eyes and doesn’t make a move to give them over. “The Impala’s too distinctive, Dean.”

“I haven’t driven her on a con since the Talbot job,” Dean protests. “Plus, Bela’s in England now.”

“Keeping tabs?” Jo asks as she digs around in his pocket for the keys.

Dean looks away. “She was a good lay,” he protests, but it sounds weak to his own ears. He actually liked Bela. She was almost smarter than him and had a reckless, we-could-all-die-tomorrow attitude that left Dean exhilarated. Not to mention, she was so loaded he actually filled up his fake passport as they traveled around the world during their whirlwind year together. 

He deserved a fucking Oscar for his performance on those flying death traps. Bela never suspected he would rather drive to see Arizona’s biggest ball of twine than fly to a Mediterranean beach.

They took her for their biggest haul ever, and once Dean was done with her, Bela had to retreat back to her family (that she hated) across the pond.

Still, the bittersweet taste Bela left behind didn’t even rank against Dean’s next job: Lisa Braeden. He almost blew the whole con wide open for her. But the Lightbringer sent in his fixer to kidnap Ben the night before Dean was about to make his move, so Dean did as he was told, left Lisa, and took all her savings with him. 

He keeps tabs on her too. She had to sell her yoga studios, her car, the house she just renovated. She moved in with her sister.

After that, Dean had never been happier to spend the next six months pretending to be Jo’s brother as she conned Victor Henrickson out of every cent he had.

“Alright then.” Dean rises from the picnic table, one hand clutching the Impala’s keys and the other holding his new identity. “I’ll see you guys on the flipside.”

* * *

Dean stays the night at a no-name motel off I-90, paying with cash taken from Cole Trenton’s safety deposit box.

As tempting as the bed is after ten straight hours of driving, Dean has work to do. He drops his bag on one bed, grabs his folder, and gets to reading.

He has Crowley’s likes and dislikes, his schedule, his background, all laid out in front of him. All Dean needs to do is put the puzzle together. Match the parts of Crowley that need complementing. Challenge the parts of Crowley that need a puzzle to work through. For this con, Dean'll stick to his strengths, playing loyal but dumb. Crowley, by all accounts, is a smug son of a bitch with a superiority complex bigger than the Pacific Ocean. 

The next day, Dean gets back on the road and takes a small detour to one of his storage containers outside Toledo. Inside lie the tools of the trade: racks of clothing in every style, drawers of disguises, and a file cabinet full of emergency cash and fake IDs.

Dean dumps the rest of his stolen cash from Cole into the emergency supply, and rifles through the clothes to pick out Michael’s new wardrobe.

No glasses this time. He skips the wigs and prosthetics too.

Instead, he grabs all the suits he can find and a mountain of button downs, most still in their plastic packaging. Time to ditch the J Crew for Brooks Brothers - less suburban dad, more corporate douche. He picks out a couple of colorful ties he actually likes, stuffing them in his bag with the boring shades of red, blue, and grey.

Dean grabs an electric razor – Michael should look rugged, not homeless.

By the time Dean is navigating through darkened LA streets three days later, he’s ready to collapse. He parks in front of the address marked in his folder. As usual, the Lightbringer set him up in a simple one-bedroom, fully furnished. It'll be his new home for the next six to ten months, if everything goes according to plan.

Once everything is unpacked, Dean drops onto the couch in the living room, utterly exhausted. He picks up his pitiful photo album – the first step in his new-place ritual - and gently flips through the stack of pictures, held together with a paperclip. 

They’ve been all across the US, shoved in the bottom of countless go-bags, spilled on, nearly torn apart on several occasions. His parents smile, frozen, out at him, standing in front of the Impala. They’re laughing and making silly faces with Dean held in their arms.

After Mom died, Dad took them everywhere, chasing seasonal jobs he could barely hold down. He’d disappear for days or weeks at a time to go off on a bender or drum up a new hustle. Dean learned all the basics from him – how to spot a good mark, how to be invisible in a crowd, how to lift wallets, watches, and phones.

The first month of his junior year, Dad left and never came back. Sam needed money for textbooks and movie tickets, not to mention a roof over his head and food. Dean sucked at school, but he didn’t suck at stealing, so he dropped out to grift full time.

Dean's life took a turn for the worst when he tried to scam one of the Lightbringer’s own gang, doing a small job in Lincoln. After getting his ass kicked six ways from Sunday, he got hauled in front of the Lightbringer’s second-in-command, Lilith. She invited him to join and really put his talents to use.

In that moment, Dean could only think of Sam, asleep in their tiny apartment in Topeka a couple hours away. Waking up in a few to go to school.

How long would he wait for Dean? How long until he thought Dean abandoned him like Dad did? How would he get by without Dean to watch out for him?

So Dean said yes. One year of service for the Lightbringer, and then his debt would be paid. He’d be home free.

Eleven months later, Lilith got to Sam. Caught him in a bad place, made Sam sign up too, and Dean knew he was in it for life.

Dean drops the photos and hides them underneath a heavy coffee table book displaying the wonders of the Grand Canyon.

Fuck, he should stop doing this routine. Always gets him maudlin. He needs to focus on the present, on the job that starts tomorrow - not his crappy childhood. 

He pulls up an episode of Dr. Sexy and grabs a drink.

* * *

Dean spends most of the daylight hours scoping out Crowley at the consultancy firm. He slicks his hair back and puts on his best suit to blend in as he flirts with Crowley’s assistant, a nervous-looking young man named Kevin Tran, and avoids Crowley like the plague. It’s not hard. Crowley doesn’t really seem to keep his voice down and can be heard from across the floor.

Kevin, apparently, has no loyalty to his boss. Hates him, actually, judging by the way he spills about Crowley’s habit of firing people in public and engaging in screaming matches with the door of his office wide open.

“So why are you working for such a douchebag?” Dean asks, eyebrows raised behind the wire-rimmed reading glasses picked up at Walgreens an hour ago.

“Pays well,” Kevin says with a shrug. “Princeton wasn’t cheap,” he adds with a hint of pride.

Dean nods appreciatively. “And you want to go into financial consulting?”

Kevin dithers around his desk, shuffling papers and tapping a couple of times on his keyboard. “I thought so, but now I’m not so sure. Everyone here…” he lowers his voice, “is so not what I pictured.”

“What’d you think it’d be like?”

Kevin throws his hands in the air. “I don’t know – not this terrible. It’s like torture every day,” he hisses, “watching all these people come in and get talked into crap deals while the higher ups treat themselves to seven course meals and trips to Aspen.”

Dean claps him bracingly on the shoulder. “Welcome to America, new grad.”

Kevin huffs and grabs his tablet. “Great.”

“Look,” Dean says, his tone serious, “You’re going to find shitty people everywhere and shitty work everywhere too. A word of advice? Find for someone good and stick with them. You’ll be amazed at how much you can take when you’ve got someone like that on your side.”

“Uh, thanks.”

“And if your boss is that big of an asshat,” Dean says as he steps back, “I would quit. A smart Princeton grad like you? You’ll find something else in no time.”

Kevin sighs and stands up. “I tell myself that every day,” he says grimly.

Dean watches Kevin go, a small frown on his face. Crowley’s office is just around the corner, and he can already hear the yelling.

Dean rubs a hand to his temples. A headache is coming on, and his stomach is flip flopping with dread. He can only imagine Crowley sitting behind his desk like a well-fed spider in the middle of a web, jerking this thread and that one, playing with his food like only the rich and mighty can. 

Dean whips out his phone on the way out of the bank.

 _Dean 10:04  
_ _How’s the job search for Crowley’s PA going?  
_ _Kevin’s a nice guy. Find him a good one.  
_ _Princeton grad, hates the firm and working for Crowley_

 _Charlie 10:04  
_ _Aww did you make a friend?_

 _Dean 10:04  
_ _Shut up_

_Charlie 10:05  
_ _On it  
_ _A “career advisor” will be contacting him tomorrow_

_Dean 10:05  
_ _Thx_

* * *

Wednesday morning dawns too early. Dean is technically free until his job interview at Crowley’s firm at two in the afternoon, but he’s the type of guy who will sleep ten, twelve hours in one go if he lets himself. Sure, he can survive on four hours, and did for years, but it’s not fucking fun.

He steps outside, and the balmy air of spring in Los Angeles nearly puts him right back to sleep again. At least the air conditioning in the coffee shop hits Dean like a slap to the face. Blinking, he looks around.

There are only a handful of people getting coffee at this late hour of the morning at Hallowed Grounds. A few twenty-somethings, headphones on and faces buried in their computer screens, sit at the counter by the window. The loudest chatter comes from a group of soccer moms in leggings and jogging gear with immaculate makeup. They take up two whole tables.

A waifish redhead in a yellow sundress waits by the pickup counter. As he gets closer, he can’t help the appreciative once-over he gives her. She smiles in response, and, yeah, Dean’s still got it.

A tourist – he has to be with that v-neck – lounges at the nearest table, a tiny cliché cup of espresso cooling in front of him. He tips his sunglasses down as Dean walks by, and Dean nearly trips over one of his extended legs as he doesn’t watch where he’s going.

Dean gets in line behind the only person waiting in front of the bar, a man in a boxy suit squinting at the menu board above baristas’ heads like it’s the Rosetta Stone.

Dean waits for second, his usual morning exhaustion warring with impatience for caffeine. “Hey,” he says, tapping the guy once on the shoulder. “You want to wake up or actually enjoy it?”

The guy turns around.

Christ, that’s some blue in those eyes. 

Dean clears his throat, and now the guy is staring at Dean. He blinks a couple of times, a hint of panic in his startled expression. 

“Excuse me?” he says - growls really, with that lower than low voice. Fuck, Dean could listen to this guy read the phone book.

Dean, who takes no small amount of pride in his inability to be shaken up by the unexpected, musters up a relaxed smile. “I said, do you just want the caffeine or are you looking for something that actually tastes good?” He raises a hand to gesture to the menu board.

“Oh,” the man says, glancing nervously around as if for backup. And damn, Dean hasn’t flustered someone this badly in awhile – at least, not outside of a con. “I don’t know.” He bites his lip. “I was, um, waiting for someone, I guess.”

“Then you’ll want to enjoy it,” Dean says to the strange dude who has apparently never been in a coffee shop… or outside his own office, judging by the completely unnecessary trench coat he has slung over his arm in Los fucking Angeles at this time of the year. “You can’t go wrong with an iced coffee on a day like this,” Dean advises. “Or maybe a flavored latte if you don’t like the taste of coffee.”

“I – yes, I suppose.” The man’s eyes flick over Dean’s casual jeans and flannel combo. “Do – do you work here?”

“What?” Dean asks, taken aback. “No, I’ve never been here before.”

“But you know…” the man drifts off, tipping his head back towards the menu.

“I’ve worked in places exactly like this,” Dean says with a shrug. “Barista, bartender, waiter, dishwasher – as long as I can work with my hands and you don’t need a fancy degree, I’m your guy.”

“I’m not looking for something sweet. Can you advise?”

“Get an iced latte,” Dean says. He taps the back of two fingers against the man’s suit jacket-clad arm. “You’ve gotta be hot in that getup.”

“It’s for work, unfortunately,” the man admits, the corners of his mouth turning up in a slight smile. He finally steps up to the counter and orders an iced latte.

But before he can get out his wallet, Dean steps up. “I’ll get his and a double americano,” he says, knocking the man’s elbow out of the way as he offers the barista a crisp twenty instead. “Keep the change,” he says with a wink.

Blue eyes narrow, accusatory. “You didn’t have to do that.”

“Call it insurance,” Dean says loftily as the barista rings up the order. “Just promise me that if you don’t like it, you won’t dump it in my lap.”

“I wouldn’t do that.”

“How would I know?” Dean asks, eyebrows raised. “I just met you in a coffee shop. Hollywood says you’re probably my soulmate or an axe murderer.”

A cough in front of them gets Dean’s attention. “Name?” the barista prompts with an eye roll.

Dean almost gives his real name, but he snaps his mouth shut in time.

“Cast-” the man says in the middle of Dean’s silence. “Just Cas.”

“Alright, Cas,” the barista says as she hands their empty cups to her colleague at the espresso machine, “Your drinks will be ready over there. Have a nice day.”

They shuffle off to wait. The redhead has moved on, and v-neck is nowhere to be seen. The soccer moms must’ve left sometime while Dean was ordering. It’s strangely quiet.

“You looking for someone?” Dean asks, eyebrows raised as Cas gives the coffee shop a second sweep in five seconds.

“My partner,” Cas says, still distracted. “She was supposed to be here.”

Dean squashes down his disappointment and gives himself a little mental shake to get his head screwed on straight. Dean has a con to pull off in four hours. He has no business getting involved with hot but clueless guys in coffee shops. “What’s she look like?” he asks instead.

“Caucasian female, five-seven, in her early 30s,” Cas rattles off. “Red hair.”

Dean holds back a snicker. That doesn’t sound how someone describes a romantic partner. “I think she left, dude. I saw her when I got here.”

“She left?” Cas repeats incredulously, actually spinning around to get a 360 view, as if she might be hiding behind one of the decorative vines climbing up the far wall.

“Yeah, sorry,” Dean says. “Maybe you could text her?”

Cas nods once and pulls out his phone. His face falls as he unlocks his screen. “She did leave,” he says, his voice laden with disbelief. “But why?” he asks in an undertone, almost to himself.

“Did she give a reason?” Dean asks.

“She says I can handle the meeting by myself.” Cas’s mouth deepens into a frown and he glances up at Dean. “That’s not what we agreed upon.”

Dean grimaces in sympathy. “That’s a shitty thing to do, leaving you to handle all of it by yourself with no heads up. If one of my partners pulled that crap on me, I’d be pretty pissed.”

Cas’s sigh is cut off by the barista calling, “An iced latte and double americano for Cas?”

“What time’s your meeting?” Dean asks as he grabs his drink. “I can wait with you, if you’re after company or something.”

“I – ” Cas breaks off, his jaw going slack. His brow furrows as he glances down at the dark screen of his phone. He looks back up at Dean. “You would do that?”

“Sure,” Dean says. “I don’t got anywhere to be for a while.”

“Thank you.” Cas reaches for his iced latte. “If you’re going to join me, would you mind giving me your name?”

Dean laughs. “Michael,” he introduces, sticking out his hand not holding his drink. “Michael Smith. It’s nice to meet you, Cas.”

Cas smiles. “You as well.”

* * *

“Hey,” Jo says as she lets Dean into her apartment.

The front door opens to a small entryway, and beyond is a large living room area with a kitchen setup along one wall. A sturdy wooden table, laden with Charlie’s multi-screen monster computer, divides the space.

“Got caffeine,” Dean says, holding up the to-go tray from Hallowed Grounds. Standing over the coffee table in the living room, he divvies up the haul - a mocha to Charlie and iced coffee to Jo.

“You were supposed to be here thirty minutes ago,” Jo says, scowling as she drops back down into her seat on the couch.

Dean takes the free armchair across from the blank television set. “It was busier than I thought it would be.”

“At eleven on a Wednesday?” Jo asks, eyebrows raised.

“LA, man.”

“Are you ready for the interview?”

“Sure am,” Dean says with a cocky grin. “Test me. Go on.”

Charlie calls out from behind her screens, “What’s his favorite drink, Dean?”

“Craig scotch, aged 30 years,” Dean says promptly. “I have a bottle of it in my apartment.”

Jo smirks. “Name of his dogs?”

“Juliet and Ramsay.”

“Where’d he grow up?” Charlie tries next.

“Scotland.”

Jo gapes, her next question forgotten. “Why the hell does he have that English accent then?” she asks, dumbfounded.

Dean shrugs. “Beats me.”

“He probably thought it sounded cooler,” Charlie says, rolling his eyes. “If you want Americans to think you’re intelligent, an English accent is the way to go.”

“Oh, can I have an accent on the next job?” Jo asks eagerly.

“Can you even do an accent?” Dean shoots back.

“’Ello gov’nor!”

Dean shudders as Charlie cackles. “Never do that ever again,” he groans, chuckling despite himself.

Jo sucks on her iced coffee mutinously. “You all suck. What’s the intel on Crowley’s family, Dean?”

“Rowena, step-mother,” Dean recites. “Father died when he was young. An ex-wife MIA. Ditto with their son, Gavin.”

“I’m working on it!” Charlie calls. “They’re in South America. Somewhere. I’ll get back to you.”

“I’m pretty sure estranged family isn’t first-date material,” Dean snorts. “If you can, let me know if they’re dead or something by the third date.”

“You got it, bro.”

Jo tries, “Last relationship?”

Dean grimaces. “With a client’s son. Set up by the client himself, which, gross. The pair of them left Crowley and his firm when they split. Wasn’t pretty.”

“He lost twenty million dollars of business,” Charlie says sagely.

Jo whistles. “No wonder he’s been out of the dating game.” She leans over and reaches out to pinch one of Dean’s cheeks like an elderly maiden aunt. “But that’s not a challenge for our widdle Deanie here.”

“Knock it off, asshole.” Dean jerks out of her grasp, rubbing his face.

Jo guffaws, nearly toppling over her half-empty iced coffee. She digs around in her pocket and pulls out a set of keys. “Here,” she tosses them in Dean’s lap. “Keys to his place.”

“You got ‘em already?” Dean asks, eyebrows raised.

Jo smirks. “Got the job yesterday. After the most ridiculous interview process for a _dog walker,_ but whatever.”

“Now Jo has access to Crowley’s house, I’ve been working on getting us a workaround for his security systems. He’s a paranoid bastard,” Charlie says cheerily, “but I’ll get in eventually. I promise I won’t spy when you stay over, Dean.”

Dean scoffs, disbelief evident. “I know you like to watch, Bradbury.”

“Aw, you got me.”

Jo says loudly, “I also got keys for you.”

“Alright!” Dean says, slapping his knee. “House party time? I bet Crowley’s got a killer liquor cabinet.”

Charlie shakes his head and checks her watch. “Dean, you’ve got maybe an hour before you should head out to get ready.”

“Probably closer to forty-five,” Dean muses. “LA traffic’s a bitch.”

* * *

Dean gets to the firm’s building ten minutes early, carrying a douchey distressed leather satchel with copies of his resume (fabricated by Charlie), cover letter, and tablet. He doubts anyone will remember him from three days ago – then, he had stalked in wearing his best tailored suit and the fake glasses. Now he’s in an off-the-rack that's an inch too long in the leg. It’s not something Dean gives two shits about, but Crowley seems the type to notice, if his tweets about his last tailor mean anything.

Dean gives himself a little shake as he gets in the elevator to the right floor, straightening his spine and pasting on his best nervous-but-excited smile. He breezes past the dyed blonde at reception, who barely acknowledges him. Kevin’s desk is empty, of course, so Dean walks straight for Crowley’s office.

“Who the hell are you?” are the first words out of Crowley’s mouth. He sits behind his desk, wearing a black suit and black button down with a steel-grey tie. He doesn’t sit up as Dean approaches, or make any move to stand. Instead, he regards him coolly as Dean hovers awkwardly in the doorway.

Dean swallows, shifting his weight from foot to foot as if he’s too taken aback to muster an answer. “I’m here for the personal assistant position?”

“Well you’re a damn sight nicer than Kevin,” Crowley says, gesturing to the seat in front of his desk magnanimously. He gives Dean another once-over. “Kevin had daintier hands, though.”

“Sorry?”

“Don’t be,” Crowley says, lounging back in his chair like it’s a throne. “Big hands have big perks.”

“I – uh, haven’t thought about it.”

“Well, then, _Michael,”_ Crowley says, straightening. “Let’s get down to business, shall we?”

The interview goes down as smoothly as a glass of Crowley’s favorite scotch. Dean sinks deeper into Michael as he tells stories about his “work history.” Each anecdote emphasizes his loyalty to his superiors. They would have been lost without Michael to work late nights. Their reputations would’ve been ruined if Michael hadn’t turned up last-minute with the missing spreadsheets. They would have been hauled off for conspiracy without Michael’s ironclad alibi.

“I need absolute discretion from my employees,” Crowley says as Michael finishes up his last story.

“Of course! Nothing is more important to me than your wellbeing – I mean,” he stammers, “the firm’s wellbeing.” He averts his gaze, biting his lip.

Crowley lets Michael stew in his supposed slip of the tongue for a long moment. “I’m surprised you’re still a personal assistant,” Crowley says eventually, tapping a finger to the printed resume lying on his desk. “With your credentials, you could be halfway to _my_ job.”

Shit.

Michael sucks in a slow breath as he frantically scrambles for an answer. “I don’t want your job – no offense,” he amends quickly. “I like being an assistant. Fewer ties, you know? I don’t like to settle down in one place for too long.” He lifts one shoulder in a half-shrug. “Restless spirit, I guess.”

Crowley purses his lips. “Right.”

And now Michael is losing him. “I didn’t grow up in one place, either,” he adds. “Military brat. My dad’s job took us everywhere, and I hated it then, but now I guess I still can’t get used to the idea of staying put.” He leans forward in his seat, meeting Crowley’s gaze squarely. “I’ve had a couple missed opportunities here and there – my last job, in Cicero, I thought for sure that was _the one_. But I got that itch, and there wasn’t much of a reason to stay, you know?”

“I see,” Crowley says as he lays his hands palm down on the desk in front of him and surveys Michael with a cool eye. “I’m not looking for a temporary assistant. What’s to tell me you won’t cut and run after six months? A year?”

Crowley will appreciate a challenge. Michael holds out his hand. “Give me a reason to stay, and I’ll be the best assistant you’ve ever had.”

Crowley doesn’t take it. “Give me five years. In writing. Then we’ll see.”

Michael’s proffered hand doesn’t waver. “Two.”

“Three.”

“Three it is.”

They shake on it, and Michael’s smile is blinding.

* * *

After he leaves Crowley’s office, Dean spends two hours on the phone with Charlie. He debriefs her on the interview, and Charlie gives him a quick run-through of how the firm’s internal systems work. After all, Dean has to spend time at work getting close to Crowley, not navigating out reports and invoices.

Michael will be the easiest employee to onboard Daimonion has ever seen.

Dean gets back to his empty apartment close to midnight, stomach full of a fast food meal he picked up on the drive over. He has enough brainpower left in him to strip and shower, but he passes out as soon as his head hits his pillow.

Dean formally starts work the next day, since Crowley has apparently been in dire straits since Kevin left him high and dry by quitting dramatically on the spot.

Dean stops by Hallowed Grounds again before he heads to the office and is only slightly disappointed not to run into Cas. 

Crowley raises his eyebrows as Michael deposits his second coffee on his desk. “What’s this?”

“Coffee,” Michael says. “Cappuccino.”

Crowley draws it closer and takes a small sip. He looks up at Michael, still standing over his desk. "My favorite. How did you know?”

Michael shrugs. “Lucky guess.”

“Bullshit.”

He grins. “A good assistant never reveals his secrets.”

“Cheeky,” Crowley scoffs, but Michael takes the small smirk to mean he’s impressed.

Michael returns to his desk, satisfied. His good mood doesn’t last long. Ten minutes later, Crowley barges out of his office to demand the financials for Styne Associates and doesn’t let up on the constant orders until nine at night. Thank god for Charlie playing backup assistant at HQ, or Dean would have fallen behind by lunch (which he skipped).

The next day is more of the same, with Crowley riding Michael’s ass to hell and back. Michael does whatever he’s told and takes it all with a smile. In the evening, he actually makes it out of the office in time for a late dinner and treats Charlie to Chinese food to make up for all the crap he’s saddled her with.

Dean drags himself out of bed on Friday morning and stumbles down the street to Hallowed Grounds. He probably should have kicked Charlie out an hour earlier, but he was so relieved to see a friendly face he couldn’t bring himself to cut it short.

Hallowed Grounds is packed, as Dean had expected at 7:30 in the morning. He stands in line, idly checking his emails – ninety-nine percent of them are from Crowley, but there’s one from Ruby, personal assistant to Abbadon, inviting him to happy hour.

As he opens a new email to reply, someone taps him on his shoulder.

It’s Cas.

“Hey!” Dean pockets his phone, a grin spreading across his face. “You’re back.”

“I’m back?” Cas repeats, tilting his head quizzically. “I’m surprised to run into you here.”

“I live right down the street.”

Cas’s eyes dart up and down Dean. “You look… different.”

“Got a new job,” Dean explains, trying and mostly failing to squash the initial glee that Cas remembered him. “Can’t roll outta bed at ten-thirty anymore.”

“That explains why we match,” he deadpans, gesturing up and down his own suit and tie.

Dean snorts. Who would have guessed the suit-and-tie office drone is an enormous dork. “Guess we do.”

“What happened to working with your hands?” Cas asks curiously.

Dean’s brain stumbles to a halt as he flushes. Cas remembered that throwaway comment? “Trying something new,” he mumbles, giving the same excuse he gave Crowley, “The suit also came with a pay raise.”

“Well, I wish you all the success in your new endeavor,” Cas says solemnly.

The corners of Dean’s mouth tip up in a small smile. “Thanks, Cas.”

“Do you come here often?”

Dean freezes, biting back his usual retort to overused lines. Instead, he manages weakly, “Little early to be using the pickup lines, isn’t it?”

Cas’s expression turns bemused. “A pickup line?”

Dean’s mouth opens and closes and opens again. “That’s the oldest one in the book,” he says eventually.

“Oh,” Cas says. He swallows. “I didn’t know that.”

“You didn’t?”

“I don’t get out much.”

“Clearly,” Dean mutters. He takes heart that Cas wasn’t offended that Dean thought he was coming onto him. Then again, this is LA, not bumfuck, Kansas.

Cas shifts his weight from foot to foot, peering over the heads in front of them to the counter. He glances behind him. “My partner is waiting with a table, if you’d like to join us,” he says nervously. “I’d like to continue our conversation from last time.”

He smiles, and Dean’s such a sucker for nice eyes and a pretty smile. 

Dean really should refuse. He tries to get to the office a good half hour before Crowley, to put out any fires that sprang up overnight. But Cas is standing right there, looking impossibly earnest, like he really wants to talk to _Dean,_ and nobody ever wants to talk to Dean – all they ever want is Malcolm or Kurt, or Alonzo (don’t ask).

And yes, Dean introduced himself to Cas as Michael, but Michael-with-Cas was as close as Dean ever got to being himself with anyone outside of Sam, Jo, or Charlie in a long time.

“Yeah, I think I can spare twenty minutes,” Dean says, his throat dry. He pulls out his phone to text Charlie to watch his email and take care of a few things for him.

“Good,” Cas says, relieved. He steps up to the counter and hands over his card. “An iced latte and a double americano please. For Cas.”

Dean tries not to be too pleased that Cas remembered his coffee order. For all he knows, Cas could be the Rain Man of coffee orders.

* * *

Cas was playing wingman. The whole time.

Dean’s good mood from running into Cas at Hallowed Grounds evaporated a while ago, drying up faster than a sundae in the Sahara. He surreptitiously checks his watch as Anna, the redhead from before, touches his arm for the third time in fifteen minutes. 

His spidey senses are pinging subtly; something is not quite right with her - hardly news-worthy, though, to Dean. After the life he’s led, he can pick a pickpocket out of a crowd in a glance. Give him ten minutes with another con artist, and Dean will have their number in five. Dean is pretty positive Anna isn’t a ginger Frank Abagnale Jr., but whatever she has up her sleeve is enough to warn him not to get involved.

Dean hasn’t misread a situation with Cas so badly in a while – years, maybe. As Anna keeps talking, Dean’s gaze keeps drifting to Cas, sitting next to the window, barely saying a word. Cas has been staring out onto the street, people-watching, since apparently strangers are far more interesting than conversing with Dean for one more minute.

Dean takes a bracing sip of coffee. “It’s almost eight - I have to go,” he says, standing up. “Work in ten.”

Anna’s face falls. “Of course! I’m sorry for keeping you, blabbering on.”

“Don’t worry about it,” Dean says with a forced smile. “It was nice to meet you, Anna.”

“You too,” Anna says. “I-” she breaks off, biting her lip, “-can I get your number?”

Dean hesitates, and Anna’s face falls further. He tries, contrite, “I’m really sorry. I just don’t think I can do a relationship right now. I just moved to LA and started a new job.”

“I completely understand,” Anna titters.

By her side, Cas nods sympathetically.

“Right, well,” Dean says, jerking his head towards the door. “See ya ‘round.”

He beats a hasty retreat, his apologetic smile dropping from his face as soon as the door slams behind him. He glowers his way past security in his building.

At his desk, Dean sits and breathes for a moment. He's got to get a fucking grip. _This_ is his goddamn job. He can’t be mooning over a random man he met twice in a coffee shop. He has to remember: it’s not only his ass on the line if he fucks up, but Charlie’s, Jo’s, and Sam’s too. The Lightbringer singled Crowley out personally. Bumped him up the line to the top spot. Dean can’t afford distractions.

He closes his eyes, inhaling deep, as he lets Dean fall away and climbs into Michael’s head.

He is Michael Smith, a scarily adept personal assistant with a very inappropriate crush on his boss.

For his first order of business, he spends a couple minutes furiously catching up on emails and tersely accepts Ruby’s invitation to happy hour. At least Crowley hasn’t arrived yet, a small miracle. Michael ducks out at the last possible moment to grab a cappuccino from the café on the first floor of the building, dropping it on Crowley’s desk just in time to bump into Crowley on his way in.

“Sir,” Michael side-steps out of the way, pasting on his best smile, “Good morning.”

“Is it?” Crowley snarks as he throws himself down in his chair. “I don’t see why it’s so great.”

“It’s Friday,” Michael says breezily, pausing in the doorway. “Fridays are always the best days of the week, everyone knows that. Apart from the weekends, of course. Do you have any fun plans?”

“Can it with the small talk, Smith,” Crowley says wearily, pinching the bridge of his nose as he breathes in deep. “I know you don’t really care.”

Michael frowns, turning a little on his heel to face Crowley fully. “How do you know that?”

“Because nobody really does. This is financial consulting. Not the bloody Peace Corps.”

“Just because you might not care about your coworkers doesn’t mean they don’t care about you,” Michael says, drawing back as if offended by Crowley’s brusqueness.

“Hah!” Crowley snorts derisively. “I know they don’t.”

Michael waits for a beat before asking, “Are you okay?”

“Don’t you have files to play with?”

“They’re not going anywhere,” Michael says evenly. “But you seem… off this morning.”

“Brilliant powers of deduction, you have,” Crowley says, his voice dripping with sarcasm. “Makes me think Mummy and Daddy didn’t bribe your way into Yale after all.”

Michael takes a full step back, hurt splashing all over his face before he forces his features into a carefully blank expression. “If you really want to know - which I suspect you don’t - I went to Yale on a scholarship,” he says in a small but firm voice. “I worked my ass off to stay there, with no help from my parents, since they passed when I was fourteen.” He straightens, glaring with watery eyes at a point over Crowley’s left shoulder. “If you’ll excuse me.”

He marches out of the office, not pausing as he hears Crowley mutter a heartfelt, “Bollocks,” to his back.

Michael’s entire morning goes by uninterrupted. He gets an unusual amount done, unsurprising since Crowley doesn’t stop by with additional tasks. In fact, he’s only asked Michael for one report by the time the lunch hour rolls around.

Michael sends an email to Crowley letting him know to expect him back at his desk in 45 minutes and has just slipped into his suit jacket when Crowley himself appears.

Expression unreadable, he barks, “We’re going out. Get your things.”

Michael doesn’t move. “Out where?”

“To lunch.”

Michael slowly grabs his satchel. “Yes, sir.”

* * *

“I’m going to do you a favor here, Smith,” Crowley says, sipping on the most expensive glass of scotch on the menu and picking at his roast chicken.

“Sir?” Michael asks, stomach clenching uncomfortably around his bleu cheese, walnut, and cranberry salad. 

“Your whole caring schtick? Better nip it in the bud.” Crowley takes a long sip of his drink. “It shows weakness. And everyone else,” he gestures around their table, “sooner or later, will smell blood in the water. Sharks, the whole lot of them. They’ll eat you alive.”

“I don’t think I can do that.”

“Honestly, I don’t understand how you got this far.”

Michael sends him a pointed look. “Maybe _by_ looking out for my friends. Ever think of that?”

“I’m your boss, not your friend,” Crowley corrects with a frown.

Michael snaps his mouth shut and looks away. He swallows once, Adam’s apple bobbing. “Right, of course,” he mutters.

He hears Crowley sigh. “Listen to me, Mikey. This is a cutthroat world. You think I got where I am by being cute and cuddly?” He doesn’t wait for an answer before continuing, “You bet your arse I didn’t. I clawed my way to the top, and that’s how I stayed there. You can’t trust anyone around here, not even me.”

Michael stares down at his salad. “I don’t believe that’s true.”

“Then you’re being naïve,” Crowley says, as he ruthlessly stabs a piece of chicken.

“I just think there has to be another way.” Michael looks up, catching Crowley’s gaze. “Having people out there watching your back isn't a weakness. Ever hear the phrase, no man is an island?”

“How about, three people can keep a secret if two of them are dead?” Crowley volleys back. “If we’re trading clichés.”

Michael shakes his head. “You must be very lonely.”

Crowely’s eyes flash dangerously. “Says the man who doesn’t stay in one place for more than twelve months.”

Michael stiffens. “That’s by choice.”

“And you think my lifestyle isn’t?”

Michael spears another forkful of salad and chews angrily.

Crowley’s eyes dart around the restaurant like their coworkers will pop out from under the tablecloths or behind the lacquered walls at any moment. “People in this industry will use anything to bump up the bottom line. That story about your parents - you don’t want to know what somebody like Alistair could do with that.”

“But that’s personal,” Michael protests.

“Nothing is personal. Everything is business,” Crowley says with a sage air slathered with pompousness. He raises his eyebrows, casting Michael an appraising look. “Have you ever considered that you’re in the wrong industry?”

Michael shakes his head. “No.”

Crowley takes a sip of his drink, sighing a little as the alcohol goes down smoothly. “You’re quite a puzzle, Mikey. A nomad who just wants to love everybody but doesn’t stick around long enough to do so.”

Michael ducks his head, biting his lip like Crowley’s caught him in the act.

“I don’t like puzzles,” Crowley cuts him off flatly. “I like straightforward people who do what I tell them.”

“You like controlling them,” Michael corrects. “People who think out of line are harder to control. But what you don’t get is everyone has hidden depths. Sometimes, they just don’t care enough about the job to act on them.”

Surprisingly, Crowley doesn’t take offense. His eyes narrow. “Perceptive.”

“That’s what you’re keeping me around for,” Michael says in a knowing tone. “I can’t predict problems if I don’t have a good sense of people.”

“And what do you sense about me?”

Michael meets Crowley’s expectant gaze. “I think you want to get close to people, but you don’t let yourself because of the job, or something that happened to you…” he drifts off, pushing a few stray leaves to one side of his plate. “I think we’re alike in a lot of ways.”

Crowley gives him one last penetrating look before downing the rest of his drink. “Take my advice or don’t. I’ve been in this business a lot longer than you, and I could teach you a few things.”

“Yes, sir.”

* * *

On Saturday morning, Dean drags himself to Charlie and Jo’s. He makes a beeline for the couch and flops down, groaning. He shuts his eyes behind the sunglasses he hasn't bothered to take off even though he’s indoors. “Jesus Christ, I’m getting too old for shots.”

“Or you’re a wuss. You’re barely in your thirties,” Jo snarks as she closes the door behind him.

“Bite me.”

“Here, dude,” Charlie’s voice comes from above him.

Dean squints, and Charlie’s red hair and earnest face comes into focus. Shortly followed by a bottle of Gatorade and a breakfast sandwich. Dean grabs both. “I fucking love you, man,” he says between bites.

“Feeling better?” Jo asks, and Dean can hear the smirk in her voice.

“A little more human,” Dean says as he wipes his mouth with the back of his hand and unscrews the cap of the Gatorade. He sits up to take a long pull. “I forgot how much normal people drink.”

“You couldn’t have poured a couple out?” Charlie asks as she sits back at her table.

“My bad,” he says sarcastically. “The bar didn’t have any strategically placed ficuses for my ten shots of Jägermeister.”

Jo gapes. “You had ten shots? In one night?’

Dean lays back down. “Maybe more like seven? Dunno. Lost count after five.”

She kicks Dean’s leg lightly with her foot to keep him awake. “You good to debrief?”

“Yeah,” Dean says, hauling himself back up to a sitting position. His eyes feel too dry and his mouth still tastes like ass, but at least the nausea is fading with the electrolytes and food. He rubs a hand down his face. This is going to be a long meeting.

He relays all he learned from Ruby, the organizer of the whole thing. She hates her boss – not a surprise, since everyone at Daimonion seems to – and dreams about killing her in increasingly violent ways. More importantly to Dean, her boss also hates Crowley, because he stole one of Abbadon’s accounts after she was out sick with the flu two years ago.

Crowley has a couple of allies at the firm: Cecily from project management, Guthrie in HR, and Dar, who works in contracts. Dean chatted them all up, made friends, and got dirt where he could.

“Right,” Charlie says, matter-of-factly as Dean trails off. “Jo?”

“Not much to report,” Jo says with a shrug, “Since you’re still working on bypassing his security systems and camera setup.”

Charlie ducks back behind her screen wall, looking wan. “I’m on it,” she says, flicking unbrushed bangs out of her face. “Almost got it. A couple more days, maybe.”

“If Dean crashes and burns, we can always ransom his dogs for a million,” Jo says with a grin. “He loves those things.”

“I bet he sees them as a status symbol,” Charlie guesses. “They _are_ purebreds.”

“Nah,” Jo waves her suggestion off. “I bet he’s compensating for something.”

Dean shudders. “Fuck, I hope not.”

“I’ve hacked his phone for you,” Charlie says, “If he has dick pics, you bet your ass I can find them.”

“No.”

“You’d rather be surprised?” Jo cuts in incredulously. “Preparation is the key to success, after all.”

Dean sags back into his seat and closes his eyes. “If I wanted smartass words of wisdom I would’ve called Sam.”

“Hey!” Jo protests. “And don’t fall asleep on us now, dude. We still have a meeting to get through.”

“What else do you want from me?” Dean groans. “I probably fucked over my liver last night, and I definitely fell flat on my face at some point getting home.”

Jo snickers. “Nice one.”

They spend the rest of the morning reviewing Dean’s plan of attack for the next work week. He’s beyond exhausted by the time he collapses on his own couch in the afternoon. He orders a whole pizza for himself, and only barely manages not to eat the whole thing. He’ll hit the gym tomorrow. (Probably.)

In the evening, he has his monthly call with Sam. 

Dean calls over the first commercial break, and Sam picks up on the first ring.

“Hey, Dean.”

“Hey, Sammy,” Dean says as he puts Trebek on mute. “How’s it going?”

“Not bad,” Sam sighs, and there’s a fucking million things Dean can read into that sigh. “Work, you know.”

“Yeah, I get you,” Dean says as he kicks his feet up on the coffee table. “I got a new project last week.”

“Oh yeah? How’s Jo liking this one?”

Dean makes a face Sam can’t see. “I got the main role again, if you can believe it.”

“No shit,” Sam says, his surprise evident.

“Yeah,” Dean says as he picks at the label of his empty beer bottle for something to do with his hands. “He's a real piece of work.”

“That’s good, then?” Sam tries. “Then you won’t feel too bad when it ends.”

“Fuck no, I won’t.” Dean sags back on the couch. “How’s your job going?”

“Fine, still on the same one as the last time you called,” Sam says. “Toni thinks she’s almost got him roped in. They want me to play the wedding planner, if you can believe it.”

Dean snorts a laugh. “Fuck, really? You never do that.”

“I know! But this is a big one. Ketch and Toni don’t want any missteps, since you-know-who always turns up for the big day.”

“Bigger than my overseas job? With that British chick?”

“Twice that,” Sam says, “by my calculations.”

Dean whistles. “Would I hear about it in the papers?”

“Maybe,” Sam says, and Dean can hear the smile in his voice. “Toni’s a redhead for this one. Playing an Eastern European heiress.”

Dean snorts. He’d met Toni Bevell twice in his life. Both times, she’d played chaperone while he caught up with Sam, once in a BBQ restaurant in Austin and again a year later in a coffee shop in Chicago. She’d worn a sour expression like someone spit in her tea the whole time.

He makes a mental note to scan the gossip rags for news of redheaded heiresses getting married in the next couple months.

“She doesn’t have the complexion for it,” Dean lies out of spite.

“Dude, Charlie sent me those pics of the time you went platinum for that New York thing. I don’t think you can point fingers.”

Dean groans loudly into the phone. “What the fuck! Why the hell did she do that?”

“The handlers talk, Dean. I don’t know what you want me to say,” Sam says smugly.

“Fuck you,” Dean says without any heat. “Charlie better watch her shampoo bottle next time I stop by her place.”

Sam laughs. “Come on, tell me about your new job. What’s your angle for this time? Maybe I can help out.”

They talk for another hour, until Sam has to go and hack into security cameras while Ketch breaks into the mark's summer home in the Hamptons. 

* * *

Dean spends most of Sunday moping, like most of his post-phone call days. He hits the gym for a few hours, beating the crap out of a punching bag and running until he’s ready to collapse. That night, he still can’t sleep despite his exhaustion, waking every couple hours from nightmares of Sam being hauled in front of the police and locked away for life, or, worse, dragged in front of the Lightbringer himself.

On Monday morning, Dean lets himself snooze his alarm exactly once before hauling himself to his feet. He dresses like a zombie and almost walks out of his apartment wearing shoes from two different pairs.

Coffee. He needs coffee.

Hallowed Grounds beckons, and Dean pushes the glass door open before he remembers why he shouldn’t.

And because Dean has never had a good luck streak in his entire life, he doesn’t have time to backtrack before he spots Cas at the end of the line.

Dean shuffles in place behind him, making sure to keep his head down. He whips out his phone and scrolls through his notes for today. Crowley has a presentation for Eve Mater this afternoon, and Accounting hasn’t come through with the Q3 projections. 

“Michael?”

Dean reluctantly raises his head. “Hey, Cas,” he says. “How’s it hanging?”

Cas bites his lip. “I - well, I suppose,” he stutters. “It’s not - I mean - Mondays?”

Dean relaxes despite himself. Poor guy, it's not his fault he isn't attracted to Dean. Even though he's clearly nervous, he's still trying to reach out. Must be desperate.

Dean pockets his phone. “Mondays suck, yeah.”

The anxious furrow to Cas’s brow smooths a little. He smiles weakly at Dean. “How was your weekend?”

“Boring,” Dean says. “Had a call with my brother and went to the gym. You?”

Cas shakes his head a little. “Work, mostly.”

Dean winces in sympathy. “Ouch.”

“At least I like my job,” Cas says, and Dean hears the barest hint of a lie in his words - or at least an exaggeration.

“What’s it you do again?”

Cas glances up at the menu board as he says, “I work for my family’s organization. I manage accounts.”

“Sounds exciting,” Dean says when Cas turns back around to face him.

“Normally it isn’t,” Cas says ruefully, “but the activity has picked up unexpectedly. I just got a new assignment, and I had thought my partner and I would be working on it as a team, but she has taken a back seat.”

“So it’s only you?”

Cas hums in agreement. “Unless I mess it up irreparably and am reassigned.”

“You won’t,” Dean says confidently.

“How do you know?” Cas asks curiously. “We’ve only met three times.”

“Been keeping track?” Dean asks, amused.

Cas swallows, eyes darting away from Dean’s face. “No, of course not. That’s ridiculous.”

“Chill, dude,” Dean laughs, and maybe he wasn't entirely wrong about why Cas spoke to him that first time. “I’ve been keeping tabs on you too. You make an impression.”

“I do?” Cas asks, stunned.

“Come on, man,” Dean says as he reaches up to rub the back of his neck. “I just moved here. LA has a rep, you know? I’m no couch potato, but, damn. There’s enough good lookin’ people here to give a guy a complex.” 

Cas blinks. “I’m afraid I don’t follow.”

Dean snorts, because, really, how clueless could this guy be? “I’m just saying, you fit in here.” Dean gives him a deliberate once over.

Cas’s mouth twitches. “I’m glad I’m giving you that impression, at least. I often feel the exact opposite.”

Dean snaps his mouth shut before he says something he can’t take back. He’s the expert at blending in while never really belonging. Mostly because he’s always working a con and has to be three steps ahead of everyone else. But he never fit in when he was a kid either - usually because he was the only one in his class who worried about water bills and scrounging up extra money so Sam could wear clothes that actually fit.

At the counter, Cas orders a latte and a double americano.

“I can pay for my own coffee,” Dean says, more playful than reproachful. “I have a real job now.”

Cas bites his lip. “I know,” he starts before he looks around, agitated, “I didn’t - you can pay me back next time. It’s easier on the baristas if they have to take care of one customer instead of two. We’re in the middle of the morning rush. They are undoubtedly working at maximum proficiency.”

“I guess so,” Dean says with a grin. If Cas doesn’t want to admit the real reason he keeps buying Dean’s coffee, Dean can get it out of him next time. He’s well versed in the long con, after all. Maybe Cas is a closet case.

Even if he isn't, Cas still brightens up Dean’s morning. If they only wind up friends before Dean skips town, Dean can be happy with that.


	3. The Play

**Summary for the Chapter:**

> Dean doesn’t know what to expect before his date with Cas. Hell, he doesn’t even know what to wear. His closet is entirely filled with douchey suits and boring button downs.
> 
> He gets in Baby ten minutes behind schedule and blasts Zep on the way over to the restaurant. To drown out his nervous thoughts, he sings along, obnoxiously loud. The long drive calms him, and for once he’s grateful for the LA traffic.

Work slogs by. The only pleasant parts of his days are meeting Cas in the mornings, where he is some weird, in-between version of himself, dressing like Michael but acting like Dean. Sometimes he catches himself imagining what would happen if Cas was his mark instead of Crowley, what he would say, what he would do, who he would be to seduce him to bed with a ring on his finger. 

He shoves those thoughts down deep. How fucked up is he - he can’t even fantasize about a normal relationship without bringing a con into it?

Michael nails his two-week evaluation. Crowley buys him a watch to celebrate, which, according to Cecily, is better than any of Crowley’s past assistants, who have all gotten pens.

Determined to take advantage of his momentum, Michael starts working weekends. Or, at least, starts appearing to. He shows up to the office and does half the work as Charlie plays backup assistant at her HQ to boost Michael’s productivity.

“Smith, I need to know everything there is to know about Roman Enterprises,” Crowley barks on Saturday morning.

Michael freezes in the middle of setting Crowley’s morning cappuccino on his desk. “Yes, sir.”

“Well?” Crowley throws him an unimpressed look. “That research isn’t going to do itself.”

Michael glances at Crowley before letting his gaze drop to the floor. “Are you okay?”

“What did I say about keeping things impersonal?”

“You said it might hurt me in the long run,” Michael says promptly. He swallows, swaying on his feet as if trying to determine whether or not to stay. “But I don’t think you’d do that… sir.”

Crowley inhales deeply through his nose. He levels Michael a weighty stare. “Shows how little you know about me.”

Michael straightens. “I know enough,” he says, his tone unshakeable in its conviction.

“Yes, well,” Crowley blusters, taken aback, “You’ve proven you know enough to do your job competently. So… hop to it, Smith.”

“Yes, sir.”

Michael stays late, only leaving as Crowley himself packs up for the remainder of the weekend. He checks the weather, and it’s raining.

He puts his umbrella back in a drawer after peeking over his desk to check Crowley wasn’t watching. They leave at the same time, Michael at a little bit of a run to catch up to his boss. 

Dean doesn’t want to play too hard to get. Crowley prefers people who come to him, not the other way around. The trick is to get Crowley to chase him enough to make a challenge, but not enough that he resents the effort.

Michael dawdles at the entryway, adopting a despairing expression as he turns his face up to the downpour.

“No umbrella, Smith?” Crowley asks before he opens his own.

“I left it at home.”

Crowley glances up at Michael. “I could drop you off,” he says as he gives his umbrella a little shake. “You don’t live too far, do you?”

“About five blocks up Gamble Avenue.”

Crowley holds his umbrella up high. “My driver is right outside.”

Michael’s eyes widen in surprise. “You don’t have to do that. It’s a very short walk.”

“Are you coming or not?” Crowley asks gruffly as he steps out into the rain. “Unlike some people, I cannot waffle about all Saturday evening.”

Michael ducks under Crowley’s umbrella, clutching his satchel to his front so it doesn’t get wet on the walk to the car. He lets Crowley get in first.

“We’re making a stop first, Marco,” Crowley says to the driver.

“510 Gamble Avenue,” Michael provides. He sneaks a glance at Crowley, a little stiff at Michael’s unexpected presence. He keeps himself at arm’s length. No accidental leg brushes.

“Who -” Michael breaks himself off with a cough. He clasps his hands tightly in his lap. “What has you hurrying home so quickly?”

Crowley’s mouth purses into a knowing smirk. “I have two dogs. They need their exercise, although I’m not sure they would even want to go out in this weather. I imagine you’re a cat person, Smith?”

Michael chuckles. “Not really. I’m allergic. I grew up with dogs, actually.”

“Is that so?” Crowley drawls. “What kinds? Rescues, I bet. With your bleeding heart.”

Michael shakes his head. “We had a pair of Mastiffs when I was a teenager. My dad won them in a poker game when he was between tours.”

Crowley swallows. “My darlings, they’re Cane Corsos, a close relative of Mastiffs. A beautiful breed. Enormous.”

Michael nods appreciatively. “I can’t stand smaller dogs. They might as well be cats.”

Crowley laughs. “I feel the same.”

“So it’s just your dogs waiting at home?” Michael asks as he studies his hands. Out of the corner of his eye, he watches Crowley’s smirk widen.

“Yes, just the dogs for now,” Crowley says with an air of indulgence. Like he finds Michael’s blatant fishing entertaining. 

At the end of the ride, Crowley says as Michael clambers out of the car, “I’ll see you on Monday, Smith.”

Michael turns back around. He pauses, his jaw clenching once. “Michael,” he corrects, ignoring the rain coming down on his shoulders and back.

“I know your name.”

“Then nothing is stopping you from using it,” Michael says.

Crowley frowns. “You’re getting wet.”

Michael doesn’t budge. “Please don’t keep calling me Smith.”

“The whole point of the ride was to spare your wardrobe,” Crowley complains.

“Will you?”

Crowley rolls his eyes. “Yes, Michael, just get inside!”

Michael smiles brilliantly before ducking his head and running for the door.

* * *

“You seem more tired than normal,” Cas says to Dean a week later.

Dean grunts his agreement. The day before, he worked late, conspicuously fixing a reporting problem Charlie had purposefully created over the weekend. If Dean plays his cards right for the rest of the week, he might be able to blame the error on Abbadon, Crowley’s main rival at the firm. He had to make sure to leave a clear paper _and_ email trail showing how he did it, leading to Crowley and no one else.

“Long day yesterday,” is all he says to Cas.

Cas hums sympathetically. “Do they make triple americanos?”

Dean snorts. “Only one way to find out,” he says as they shuffle forward in line.

“I don’t think that much caffeine can be healthy.”

Dean rolls his eyes. “I don’t need to get fired today for sleeping at my desk. At this point, I’d rather have the caffeine-induced heart attack. Then at least I could take medical leave.”

“Or you could get a full night’s sleep.”

“Hey,” Dean says, hands up in a gesture of appeasement. “I got my four hours.”

Cas’s eyes narrow. “The average human needs eight and a half.”

“The average human doesn’t work for my boss,” Dean says in an undertone. 

“Are they being difficult?”

“You could say that.” Dean wrinkles nose. “He’s not my worst, but he's up there, if you catch my drift.”

“At least you’ve never had to work for family,” Cas sighs.

“No, I never had that experience, thank god,” Dean says with a laugh. “If I ever had to work for my dad, I’m pretty sure I wouldn’t last a week.”

“Why?”

Dean bites his tongue as he thinks over his answer. “My dad always had high expectations for me,” he says slowly. He doesn’t add, _and I never seemed to measure up._

“At least your father clearly cared,” Cas says, the echoes of an old bitterness in his tone. “Mine was often absent. He couldn’t be bothered to convey his expectations to us at all.”

Fuck, Dean is too tired and too sober for this. He mutters, “My dad wasn’t around a lot either.”

“I’m sorry,” Cas says after a moment, and fuck it all, he sounds sincere. He doesn’t even look uncomfortable at the personal turn of the conversation. 

Dean waves off his apology. “But you make it work with your folks, right?”

“More or less,” Cas hedges. “They leave me alone, and I leave them alone, for the most part. I see my siblings far more often and, occasionally, enjoy their company.”

“Man, I wish I could see my brother more.”

“How often do you see him?”

Dean’s heart sinks. “Once a year,” he says quietly. “We both move around a lot, and it’s hard to get everything to match up.”

Not to mention, the Lightbringer was a paranoid son of a bitch who was convinced Dean and Sam would scheme their way out of his clutches (taking a good chunk of his cash with them) if allowed to meet up more. Dude wasn’t wrong, but that didn’t mean Dean couldn’t be righteously angry about it.

Ever since Dean got tapped for the big jobs after his first year - the marriage cons - he hasn’t been in a room with Sam for more than a few hours every twelve months.

“What does he do?”

“He’s in theater tech,” Dean says. “Goes on the road with the company across the US. We call once a month, at least.”

They step up to the counter, and Dean elbows Cas aside to get this one. Cas lets him with an indulgent little smile. The fucker had beaten Dean and paid for their coffee for the past two days.

They move out of the way for more customers, and Dean stifles a yawn behind his fist.

Cas doesn’t say anything for a long moment, and Dean doesn’t blame him. It’s fucking early, and they already scratched the surface of Dean’s problems. Normally that’s third date stuff. Or it would be, if Dean ever told any of his dates about his real family.

Nothing screams ‘fuck me, I’m vulnerable’ more than daddy issues.

“Michael?” By the tone of Cas’s voice, it’s not the first time he’s tried to get Dean’s attention.

Dean blinks dazedly at him, his stomach sinking as he takes in the serious expression on Cas’s face. “Yeah?”

“I was saying, I have to go now, but I’d like to keep talking to you.” He smiles softly. “Preferably when you’re awake enough to answer.”

“‘Course,” Dean says, fighting to keep the sarcasm out of his voice. “Gotcha. I’ll try real hard to get my - what was it - eight hours? And see you back here at 0700.”

Cas bites his lip. “I didn’t mean here.”

Dean freezes. “But we always meet here,” he says stupidly.

Cas's face is unbearably earnest as he says, “I was thinking somewhere we could actually sit and talk.”

Dean’s eyes go wide. “I, uh,” he fumbles, and, fuck, of course he’s not smooth at _seven fifteen in the fucking morning with no caffeine._ The ‘yes’ sits on the tip of his tongue, but his conscience holds him back - and his sense of self-preservation.

Because that sounds awfully like a date, and Dean strictly _does not date,_ unless there is something in it for the Lightbringer. Dean should be focusing on Crowley - not Cas.

Cas is just a man, a nice guy who had the misfortune to catch Dean’s eye. He doesn't deserve to have his time wasted by a liar and a con artist.

Dean hesitates, and Cas’s face falls. Blue eyes downcast, his mouth works as he struggles to find something to backtrack the conversation.

“Yeah, I’d like that," Dean says with a would-be casual shrug of his shoulders.

Cas’s head snaps back up so quickly it almost looks painful. “Yes?”

“Yeah,” Dean repeats with an ease he doesn’t feel at all.

A relieved smile spreads across Cas’s face. He reaches inside his jacket pocket and pulls out his phone, asking shyly, “Could I maybe get your number?”

* * *

Dean doesn’t mention his _thing_ with Cas to anyone. 

To his surprise, Cas texts him first, that very afternoon.

 _12:41  
_ _Are you free on Friday?_

Michael heads for the bathroom.

Hidden away in a stall, Dean pulls his phone back out. He rereads Cas’s text, his heart in his throat. 

The three-days rule is bullshit, but most people would wait a little more than _three hours._ He could rip apart Cas’s text, analyze it for hidden meanings, read subtext where there is none. He’s done it before, poured over a mark’s phone as he played their new best friend - sympathized with them and manipulated them as they picked apart Jo’s messages.

In Dean’s experience, the text tells him more about himself than Cas. 

Dean has texted marks the same day as their meet-cute. He has waited a whole week, on occasion. It all depends on the mark. How needy they are. How much validation they crave. How starved they are for a connection.

For the most desperate, Dean always texts the same day.

 _Dean 12:43  
_ _Maybe? Depends on when you want to meet up  
_ _I have a thing in the late evening_

Cas’s reply comes instantly.

 _12:43  
_ _I am flexible. When works for you?_

Dean curses quietly to himself and checks Michael’s notes for the week. He has to “run into” Crowley at his favorite bar at around nine at night. 

_12:44  
_ _Six?_

Three hours is enough for Dean to have dinner and make it to Ninth Circle. Right?

 _12:44  
_ _That works for me as well.  
_ _I’ll text you the address later._

 _Dean 12:44  
_ _Sounds good_

Michael exits the bathroom, straightening the tie he had worried loose with his fingers. He barely has time to wake up his computer before Crowley breezes past, saying, “My office. Now.”

Michael grabs his notepad and pen and hurries to follow. He closes the door behind them.

“Abbadon is getting sacked,” Crowley says gleefully as he turns around to face Michael.

“Is that good news?” Michael asks, eyes wide. “She is a senior partner.”

“Don’t play dumb,” Crowley says flippantly. “I know you did this. Take a seat.”

Michael sits, placing his notebook in his lap. “Am I in trouble?” he asks nervously.

“God no,” Crowley says, turning around and grabs a decanter from a tray in his office. He pours out two drinks. “Here.”

Michael glances down at the watch Crowley gave him after his first two weeks at the firm. “It’s barely one in the afternoon.”

Crowley rolls his eyes. “This is a celebration, Mikey. We can’t celebrate without a toast.”

“What are we toasting?”

“The first step in Abaddon’s downfall,” Crowley says with relish. “And all your efforts to make it happen.”

“It was nothing,” Michael says quietly. He raises the scotch to his mouth, staring up at Crowley through lowered lashes. He licks his lips slowly as he sets the glass back down.

Crowley reddens. He busies himself with pouring another finger of scotch. “Why did you do this? With Abbadon gone, it means things could get… volatile around here.”

“She made a mistake. People who make mistakes are liabilities.”

Crowley takes a seat in his chair and surveys Michael with a beady-eyed stare. “Liabilities are dangerous,” he concedes.

“And that is why her mistake deserved to be brought into the open,” Michael says calmly. “Our clients lie and hide things from us all the time. We should at least be better than them.”

“Right, right,” Crowley hums. “What a righteous little worker bee you are.”

Michael ducks his head. “It was the right thing to do.”

Crowley takes a hefty swallow of scotch. “You did me a favor.”

“I did?”

“What did I say about playing dumb?” Crowley asks, clearly more amused than angry. “A kingdom is never as unstable as it is in the middle of a transition of power. And you, Michael, have just knocked over one of the main supports holding this company together. Her removal will probably be in the firm’s best interests, of course. Abbadon has been getting sloppy and her bottom line hasn’t been increasing as quickly as it should be by Q3. The firm will do better with someone else in charge.”

“With all due respect, sir,” Michael says in a low voice, “I didn’t do it for the firm.”

“No?” Crowley raises his eyebrows.

Sincerity shining from his bright green eyes, Michael says, “I did it for you, sir.”

Crowley’s eyes narrow. “I see.”

Michael drops his gaze back to his half-empty glass of scotch. He traces a thumb around the rim, his breath coming a little too quickly. He tips it back and finishes it off.

“To be clear,” Crowley starts in an undertone, “This isn’t a case of _you scratch my back, I scratch yours?_ ”

Michael shakes his head. “No, sir. I’m not asking for any…” he trails off, searching for the right words, “benefits in return.”

Crowley’s eyes narrow. “I wouldn’t blame you if you were. You handed me one hell of a winning hand here, Michael.”

“I was just doing my job, sir.”

Crowley scoffs, “We both know this is above and beyond the calling of my personal assistant.”

“You’re the one who wrote the job description,” Michael says as he stands to go. “What your personal assistant can and cannot do is entirely up to you.”

He leaves Crowley with that parting thought.

* * *

Dean doesn’t know what to expect before his date with Cas. Hell, he doesn’t even know what to wear. His closet is entirely filled with douchey suits and boring button downs. He has precious few of his regular clothes. Every single pair of jeans has a hole in the knee or crotch. He chose his tee shirts from that storage unit in Toledo out of comfort, not presentability. 

Dean groans to himself for an embarrassingly long time.

Eventually he picks out his darkest jeans (the stains are barely noticeable), and a blue button down. He rolls up the sleeves to his forearms to make it look a little more casual. It’s too hot for a jacket, or Dean would have snagged his leather one for sure.

He gets in Baby ten minutes behind schedule and blasts Zep on the way over to the restaurant. To drown out his nervous thoughts, he sings along, obnoxiously loud. The long drive calms him, and for once he’s grateful for the LA traffic.

He pulls into the parking lot behind a Italian place on the edge of Downtown and takes a moment to gather himself. He checks to make sure his phone is still turned all the way off. If Cas stands him up, Dean would rather wait him out than risk anyone from the Lightbringer’s crew tracking his location.

Charlie will kill him for the gap in her data inflow if she notices, but Dean can deal with her later.

After he inhales a fortifying breath, he opens up the driver’s side door with a familiar creak of metal and makes his way inside.

The place is more upscale than Dean would ever choose for himself, but less fancy than he’s used to - what with all the rubbing elbows with bankers and financiers he’s been doing lately. 

The hostess zeroes in on him the moment he steps over the threshold. “Reservation?” she chirps. 

Dean rubs his sweaty hands on his jeans. “Yeah, under Stevens?”

The hostess beams at him as she finds the name on her tablet. “Table for two at six. Unfortunately, we don’t seat incomplete parties. Please feel free to wait at the bar or in our waiting area.”

“I’ll…” Dean jerks his finger over his shoulder in the direction of the bar. One drink can’t hurt. As long as he takes it easy during the meal, he should be sober enough to drive home.

It’s a little early for the dinner crowd, but the happy hour is in full swing. The noise of so many conversations muffles Dean’s nervous thoughts for the time being. People bustle up against the bar as Dean mills around for an opening to get to the bartender. He catches the eye of a handsome man in a waistcoat and suit pants, who obligingly inches a little to the left to make room for Dean.

“Whiskey please,” Dean says as he flags the bartender down. “Neat.” 

When the drink comes his way, he downs half of it in one swallow. 

“Long day?” the guy in the waistcoat asks, eyebrows raised.

Dean shakes his head. “Long night ahead,” he says before he tips his drink back again.

Waistcoat gives him a blatant once-over, and Dean’s spidey sense goes haywire.

He doesn’t usually set off other men’s gaydar if he can help it; he only dresses flamboyantly for certain cons. Otherwise, he would rather pass and blend in until he makes his move. But Waistcoat pegged him instantly, and that doesn’t sit well with Dean. 

“Too many plans?” Waistcoat asks casually.

Dean shrugs. “You know how it is,” he says, falling back on something generic and vague. He deliberately turns to face forward, but the guy turns with him.

“Not really,” he says. “I have a whole free night ahead. I’m Ishim.”

Dean waits for Ishim to give up, but he seems determined. He says eventually, “I’m not interested.”

“Come on, you barely gave me a chance.”

“I don’t need to give you shit.”

Ishim raises his hands, palms up, in a gesture of surrender. “Hey, I’m just being friendly. If you’re a little wound up, I bet I can help you relax more than that drink in your hand."

Dean grimaces. As if he didn’t have enough on his mind, now he has to get rid of this jackass who can’t read the signals practically tattooed across Dean’s forehead.

He opens his mouth to really lay it into him, but a familiar gravelly voice from behind the pair of them gets there first.

“I don't believe he needs any help with that,” Cas says as he elbows between the pair of them. “I’m sorry,” he tells Dean as he leans in to kiss his cheek, “I had some car trouble on the way here.”

Warmth curls in Dean’s gut and his cheek feels like it’s on fire. He turns, wide-eyed, to Cas - they’ve never so much as held hands before. 

“I’m glad you’re here,” Dean says, and he doesn’t even have to fake the breathiness in his voice. He glances around to kick Ishim out of the way for his date, but the skeezeball has already slunk off to bother someone else.

“I’m sorry I’m late,” Cas repeats.

“Don’t worry about it,” Dean says with a grin. “You’re here now.”

* * *

To Dean’s surprise, Cas walks around to pull his chair out for him. He gingerly takes a seat. “Working again on a Saturday?” 

Light purple bags stand out under Cas’s eyes, and his hair is more untamed than usual, like he’s been running his hands through it all day. He is even wearing his usual suit getup and has his trench coat slung over one arm. The untied belt just barely trails on the floor as he drapes it over the back of his chair.

Cas makes a face. “Unfortunately.”

“Glad you could get away to see me, at any rate,” Dean tries, his nerves ratcheting back up to nuclear levels now they’re at the _date_ part of the evening.

“Indeed,” Cas says as he fiddles with his napkin in his lap.

“I’ve never been here before.” Dean glances around. God, he sounds so _stilted._ What the fuck is wrong with him?

“Me neither,” Cas says, a strange heaviness to his voice. “My coworkers recommended it.”

Dean nods along, feeling a little wrongfooted for no discernible reason. Is this how most people feel on first dates? The skin on the back of his neck prickles, heat building under his collar. 

Turns out the real Dean is shit at dating without a script to follow. Go fucking figure.

“Sorry,” Cas’s voice applies the brakes to Dean’s depressing train of thought. “I am not used to this at all.”

Dean blinks. “What?”

“I haven’t been on a date in years, actually.”

“I’ve… well, I’ve been on dates,” Dean says hesitantly, imperceptibly pausing after every word to gauge Cas’s reaction, “but not with anyone I really _wanted_ to date in just about,” he laughs humorlessly, “forever.”

The corners of Cas’s mouth lift into a small smile. “We’re in the same boat, it seems.”

Dean chuckles, some of the weight of expectation lifting off his shoulders. He takes a sip of water. “What made you ask me out, then? If this isn’t your normal thing.”

Cas stares down at the empty place setting in front of him. “When I first met you, I didn’t think I would. My ‘people skills’ are ‘rusty,’ you might say.”

Dean snorts at the air quotes. “I work with smooth talkers who blow smoke up my ass all day. Trust me, it ain’t any greener on the other side.” 

Cas tilts his head as he studies Dean across the table. “If you say so,” he says, clearly not believing a word. “But you kept talking to me. It made me think I wasn’t as hopeless as I thought.”

“I mean, you’re a little hopeless,” Dean points out, his tone teasing. “You tried to set me up with that redhead.”

Cas’s eyes widen. “Anna, yes. You didn’t connect.”

Dean makes a face. “Something was off with her. I could tell.”

“You were meeting her for the first time,” Cas says, his brow furrowing. “Do most people present themselves in an honest light when they’re flirting with a potential romantic partner?”

Dean breaks down into laughter. “Hell no. That’s a one-way ticket to a brush off and fake number.”

“Then what did she do wrong?”

“Dunno,” Dean hedges. “It’s one thing to exaggerate the good stuff and play down the bad, but I got the feeling it was more than that with her. It was a gut thing.”

Cas doesn’t seem satisfied with Dean’s explanation, if his frown is anything to go by.

“Look,” Dean says, bracing one elbow on the table to lean in closer. “You’re better off thinking about what you did right.”

“What I did right?”

“Yeah,” Dean says with a little laugh. “I got a good feeling about you. That’s why I went with you instead of her.”

The waiter appears before either of them could say much more. Dean, who hadn’t even glanced at the menu, picks the first thing he can find with real red meat in it. Michael eats too many salads, meaning Dean hasn’t had a decent fucking meal in too long.

When the waiter disappears, he turns back to Cas. 

From brief chats over waiting for coffee, Dean learned Cas is originally from Pontiac, Illinois. He came out to LA to help his family’s charity set up a branch on the West Coast. While the charity has many avenues for giving, his branch primarily raises money for under-privileged youth, sponsoring academic tutoring, scholarships, college preparation, and mentoring programs. He has several siblings, precise number and names unknown. He is on rocky terms with his parents, wealthy but distant. He commits himself to his job. It lets him live comfortably but without much of a social life.

Fuck. 

Cas isn’t a mark. Dean doesn’t need to analyze him like one.

This is a date. A _real date._ Dean can’t waste it by treating it like another job. 

And _why_ isn’t Cas saying anything? He is just sitting there, staring at Dean like he would like nothing better than to study Dean’s face for five full minutes.

“I used to steal cars,” Dean blurts before he can overthink it. “Got pretty good at fixing ‘em up too. I could take a look at yours, if you like. You said yours was acting up.”

There. Dean broke the number one rule, _Don’t talk about yourself._ Let the mark carry the conversation, and they will spill all sorts of things to a willing ear who knows to keep their cakehole shut.

Cas blinks, head tilting. “You stole cars?”

Did the restaurant amp up the heat to make him sweat? It feels like he’s back in Lisa’s hot yoga class. “I did,” Dean admits. “I was a minor, though, so I got out of any real charges.”

Cas’s eyes narrow. “If I let you look at my car, you won’t steal it?”

“Of course not,” Dean says, mock-affronted. “I’m done with my run-ins with the law.” He was done with getting caught, at least. “And wouldn’t that be a shitty follow-up to a first date? Jacking your car and selling it for parts?”

“It would be a new low for me and my romantic prospects,” Cas says gravely.

Dean cracks a grin. “We can’t have that. Plus, I’d do it for free, which is more than any of the mechanics around here will do.”

Cas sends him a pleased little smile. “That’s very nice of you. I might take you up on your offer.”

“What do you drive?” 

“A 1978 Lincoln Continental.”

Dean snorts into his glass of water. “Dude, really?”

“What’s wrong with my car?” Cas asks, a tad defensive for a guy who drives a pimpmobile. 

“Just don’t tell me you modified the hydraulics.”

Cas’s silence is telling.

Dean leans in close, placing an elbow on the table. He says in a low voice, “Aren’t you full of surprises?”

Cas shuffles in his seat, looking a little red in the face. “My brother gave it to me a couple years ago after my old car was totaled. _He_ modified them.”

“Your brother must have a sense of humor.”

Cas rolls his eyes. “Many people think so.”

“You don’t?”

Cas’s mouth twists. “His jokes - pranks - tend to slide more towards ironic rather than funny.”

“He caught you unawares a couple of times, I guess?”

Cas nods stiffly. “He’s the one who totalled my car. He gave me the Lincoln in recompense so I could get to work.”

Dean winces. “I would murder my brother if he ever touched my baby. He once put in an iPod jack while I was… outta town, and I came _this_ close to decking him across the face.”

“Your baby?” Cas asks, baffled.

“Yeah,” Dean beams. “She’s a ‘67 Chevy Impala.”

“...She sounds very impressive,” Cas says politely.

Dean takes pity on him. “She’s a beauty. I’ll have to take you on a drive some time. Show you what a real classic car can do.”

Cas ducks his head, a pleased smile playing about his lips. “I’d like that very much.”

* * *

Dean swears at the third consecutive red light he hits. Fuck this bullshit LA traffic. Jo and Charlie will kill him if he messes up this run-in with Crowley at Ninth Circle. It’s supposed to be the turning point in his relationship.

He floors the gas as soon as the light turns, taking a sharp turn onto Ventura. He fumbles around blindly in the glove compartment before his fingers close around the ostentatious watch Crowley gave him. He slips it on, checking the time and cursing.

His lips still tingle where Cas kissed him, pressed up against the Lincoln. Dean had almost doubled over laughing when he saw it, but Cas had shut him up with his mouth and a determined glint in his eye.

Dean left Cas with plans to check out the weird sound coming from under the hood whenever the Lincoln goes above 30 mph next Saturday. 

Dean cranks down his window, but the warm air flying past doesn’t do much to lessen his flushed, exhilarated face. 

He taps his fingers on the steering wheel as he checks the time again. 

When he finally arrives, Michael drops the keys to the Impala at the valet service with a stern glare. At the front door, he checks to make sure his shirttails are tucked in and his hair is in order.

The cocktail lounge smells like expensive liquor and, faintly, of cigars. The decorator could have put in more lights and a few mirrors to make the place feel less claustrophobic. The servers drift past in all black uniforms that blend in with the ebony furniture and dark walls. 

Michael picks out Crowley at the far end of the bar, drinking with a few business associates and friends Michael hasn’t technically met before. He takes a seat in the middle and flags down the bartender.

“Bout time you showed up,” Jo mutters as she places a cocktail glass in front of him and fills it surreptitiously with water.

“Nice hair.”

Jo fluffs her short black bob. “Right back atcha, Douchey Spice.”

“You haven’t been made?”

“Please, I’m a professional. And he’s not the type to look above the T-shot, if you catch my drift.”

“What?”

“Come on, we’re in Hollywood,” Jo says with a grin and an eye roll. “The titty shot. Keep up with the lingo. I’m fine. Crowley couldn’t pick his dog walker out of a lineup on a good day. Throw in a wig and glasses, and I might as well be invisible.”

Dean grimaces. “How much have they had?”

“Two rounds so far,” Jo murmurs. “They usually stick around for six or seven.”

“Great.”

“Buck up,” Jo says. “You’re a professional too.”

Dean swallows. For a brief two and a half hours, he hadn’t been.

“Get ready,” Jo says as she peeks over her shoulder. 

She knocks over his water. “Shoot!” she hisses, still loud enough to be heard. “I’m so sorry, sir! I’ll get you another right away. It’ll be on the house.”

“It’s fine,” Michael says as he stands up, shaking out his wet sleeve.

“Michael?”

Michael spins around, his eyes widening in recognition. “Mr. MacLeod,” he says. “I’d shake your hand, but-” He holds his arm out, letting a couple of drops fall to the floor.

“I understand,” Crowley says with a smile. “What are you doing here? It’s a little out of the way for you.”

Michael shrugs. “I was looking for a decent scotch selection. This place came highly recommended.”

Crowley draws back, impressed. “You’re not wrong. Scotch, you say?”

Michael nods.

“Have you ever had Craig, aged 30 years? Nothing like it.”

Michael shakes his head, and Crowley catches Jo’s attention. “Forget whatever he was drinking. He’ll have the same as me.”

Jo bobs a nod, her fake hair falling in front of her face, and turns her back to pour Michael a glass.

Crowley looks around. “Are you here alone?”

Michael sends him a searching look. “I _have_ only been here a few months, sir. There hasn’t been a lot of time for socializing,” he says wryly.

“Come on,” Crowley says once Michael has been sufficiently provided for. “I’ll introduce you to my friends.”

* * *

As the night wears on, Michael gets progressively looser with his longing looks and fleeting touches. His shoulder brushes occasionally against Crowley’s, but Michael makes no move to shy away. Neither does Crowley.

“Shots!” Michael proclaims several rounds later as Jo deposits the tray in front of their group.

Crowley’s friends all cheer.

Quick as a flash, Michael snags the shot glass at the very end of the line. “To Daimonion, long may you prosper!”

Everyone drinks. 

Michael grimaces as sugary apple juice hits his tongue instead of the whiskey everyone else tosses back. He blinks slowly at Crowley. “Do you do this every Friday?”

“Nearly,” Crowley says, an amused smile playing across his mouth. “It helps me unwind after a long week.”

“I bet I could help you… unwind.” Michael ruins the effect of his bedroom eyes by hiccuping in the middle.

Barthamus, a banker and one of Crowley’s more outspoken cronies, guffaws loudly. He slams a hand, hard, against Michael’s back. It’s just as much a gesture of friendly camaraderie as intimidation. “God fucking knows you need to _unwind,”_ Bart tells Crowley with a lewd grin. “Has had a stick up his ass for _months,_ ever since he lost that twink and his $20 million invest-”

Crowley punches him in the face.

Shocked, Michael can only watch as Bart shoves Crowley back, only for Crowley to come at him swinging again.

A security guard arrives before long, shoving the drunken Daimonion employees out of the way. “Hey, break it up!” He grabs Crowley by the arm. 

Crowley struggles, his face mutinous, as Bart gets unsteadily to his feet. “You’d better watch yourself, mate.”

“Yeah, sure, _Fergus,"_ Bart spits.

Michael throws him a dirty look before stepping up to Crowley. “I think we need a little air,” he says.

Crowley blinks. “Yes, of course,” he says as he straightens his jacket. “I’ll accompany you.”

Once they’re outside in the humid LA night, Crowley turns to Michael. “I’m sorry you had to see that,” he says in an undertone. “I’m not usually like that.”

Michael stares stonily ahead. “It’s fine.”

Crowley's brow furrows. “I don’t want this to color how you see me, Michael.”

Michael chuckles, the sound dark and strained. “It’s a bit late for that, sir.”

Crowley stares out across the street. “At the very least, I trust you will keep up your good work at Daimonion.”

Michael doesn’t say anything for a moment. “I don’t work for Daimonion, I work for _you.”_

Crowley’s jaw clenches, his expression hardening.

Michael inhales a sharp breath, his green eyes large. “And when you punched him, that was the hottest thing I’ve ever seen.”

Crowley’s head jerks around to face him. As shock gives way to understanding, he takes a step closer. “Is that right?” he murmurs, his voice barely loud enough to be heard over the traffic passing by.

Michael gulps. Eyes trained on Crowley’s lips, he breathes, “Yes, sir.”

“Fuck, I love it when you call me that,” Crowley says, his eyes dark with lust.

Dean almost throws up in his mouth. Fighting to keep his expression hopelessly infatuated, he freezes as Crowley steps in closer.

 _Wrong._

Dean’s stomach roils as Crowley pauses short of Dean’s mouth, his breath hot against his lips.

Cas - with Cas it had felt right. Cas made the first move, but it didn’t send Dean running for the Hollywood hills, panic racing through his veins.

He would give anything to be just seconds away from kissing Cas again instead.

If Dean thought the buildup was excruciating, it has nothing on the actual kiss. Crowley pushes against him aggressively, his tongue licking against the seam of Dean’s lips. He moans, and, for the first time, Dean can’t slip back into Michael’s head. He can’t do it.

Dean prays for it to be over the entire time.

* * *

The next day, once Dean has his head on mostly straight, he calls Sam from the relative safety of his own apartment. Sam picks up on the first ring.

“I’m in such deep shit,” Dean whispers into the receiver, his head in his hands.

“What kind? Are you hurt?”

“No.” Dean swallows, his throat dry. “I got my hands on another... project.”

“Already?” Sam asks, his surprise clear over the line. “Did he kick you off the old one?”

Dean starts shaking his head instinctively before saying aloud, “No, I’m still on that one.”

“Too?”

“Too.”

“Are… you hoping to get switched to your new one?”

“Fuck no,” Dean says with a humorless chuckle. “You’d call it… a personal project.”

“Goddammit, Dean.”

“I know.”

“You’ve never had a personal thing before. The closest you ever got was with that yoga instructor. Even that one was approved.”

“Yeah. This one’s not.”

“Does anyone know?”

“No. And I plan on keeping it that way.”

“Charlie will suspect something.”

“Not if you keep your fucking mouth shut. I still haven’t got her back for sharing those New York pics.”

“I won’t tell, I swear,” Sam promises. “But… you can’t keep this to yourself forever.”

“Yeah,” Dean mumbles. “I know.”

“You remember the last time I had a personal thing get in the way of a project.”

Fuck, Dean could never forget that. She’s the reason Sam never gets called up to be the frontman anymore. 

Jess was a mark like any other, back when Dean and Sam were still allowed to be on the same job. Sam was still baby-faced enough to fit in at college. He was supposed to take the lead as Dean played backup, watching out for him on the sidelines. Brady was their handler.

Sam knew what to do: get invited back to Jess’s place for Spring Break and be their inside man while Dean and Brady robbed Jess’s parents blind. They already had the blackmail ready to scare the Moores off from reporting the theft.

But Sam, who wore his heart on his sleeve, couldn’t do it. He turned down the big invite when it came.

So Dean had to improvise before Brady reported everything back to the Lightbringer. 

When the next crew finished the Moore job, they not only took everything, they released all the intel the Lightbringer had.

Jess had to drop out of college. Her father went to prison. Her mother disappeared.

“What are you going to do?” Sam asks.

“I have no fucking clue.”

“I think you already know what I’m going to say.”

“That I should drop it?”

Sam’s long silence tells Dean he was right on the money. “What’s so special about this one?” he asks eventually.

“I dunno. He’s … so far away from any of this. He’s so fucking awkward, man. And genuine - in a way I haven’t seen in a long time.”

“So he’s basically the opposite of you,” Sam says, his voice flat.

“Yeah.”

“Jesus Christ, there’s no way this will end well.”

“You think I don’t know that?” Dean retorts. “It’s all going to blow up in my face. There’s no way it won’t.”

The other end of the line rustles, and a door closes. Sam’s voice comes through, stronger but hushed, “You could take a trip to Poughkeepsie after this job.”

Dean’s mouth goes dry. “I haven’t thought of that. I didn’t think it was even possible.”

Sam’s voice drops to an undertone. “It wasn’t when we were starting out. But we’ve been at this for _years._ If you’re compromised, there are more choices than last time. Just… let me know how you want to play it. I’ll try to help from here any way I can.”

Dean smiles. “‘Course I know that. And if I do swing by upstate New York, you bet your ass I’ll send a postcard.”

“I’ll send you an email with my address.”

Dean’s eyebrows fly up as high as they will go. They’ve never exchanged emails - Sam deemed them too risky, too hackable. Phone calls only.

Thrown, Dean manages to say, “Sounds like a good idea,” before he chickens out and hangs up.

On Sunday, Dean receives an email from Wedge Antilles asking for donations to help a kid injured in a freak hunting accident. All checks should be sent to an address in Sioux Falls, South Dakota.

Dean spends the rest of the day at the gym, pounding at the punching bag until his knuckles blister and running until he can’t breathe. 

* * *

Cas doesn’t meet him for coffee on Monday morning. Dean waits an extra fifteen minutes in case Cas slept through his alarm (there has to be a first time for everything). Dean stays so long he doesn’t have time to grab Crowley's cappuccino.

Michael has a terrible day. Crowley makes Trish from HR cry and Dean has to sit there, stone-faced, as she stumbles past his desk to the bathroom to clean herself up.

Tuesday morning - no Cas.

Michael makes plans to join Crowley at his house to take care of extra work on Saturday. They will probably have dinner together afterwards. By the end of the day, Michael's face hurts from smiling so much. 

Wednesday is more of the same. Crowley fires Jarvis over taking too much bereavement time after his mom died from cancer in February and his oldest sister unexpectedly got run over a month ago.

Laying in bed on Thursday morning, Dean briefly contemplates calling in sick. He could take the day off, review the additional intel Charlie collected (not that he needs to). Pick out his date outfit two days ahead of schedule. Drink the shitty apartment-brewed coffee he’s never touched in the two months he’s been living there. 

Dean takes one look at his Keurig and turns away in disgust.

He is a fucking adult. He can get his own goddamn coffee without falling apart like a ditched prom date. Hell, he probably deserves this for all the beyond-fucked-up things he’s done to his past dates. Figures karma is a bitch.

Dean almost plows right into Cas on his way into Hallowed Grounds. 

“Christ, Cas, sorry! Wasn’t expecting you there.”

Cas looks like crap. His face is sallow and drawn, like he hasn’t seen the sun in days. His hair looks a little oily and unwashed. At least he doesn’t smell. “Hello, Michael,” he rasps.

“Woah,” Dean says, all the demands for the reason behind Cas’s absence dying in two words. Before he can stop himself, he reaches out to grip Cas’s upper arm securely, almost to verify it’s really him. He gives Cas a little reassuring squeeze. “You don’t look so hot.”

Cas grimaces and doesn’t dignify Dean with a response. He stares straight ahead at the slowly shrinking line like he could kill them all in one fell swoop if he glares hard enough.

“Are you sick?” Dean asks.

“Overworked.”

Dean frowns. “Dude, I know you work hard, but maybe you should take it a little easy for this week. You look ready to fall over.”

“I feel like I could fall over.” Cas rubs his temples tiredly. 

“Is it that new assignment?”

“What?”

“You told me you got a new assignment… about a month and a half ago?” Dean reminds him. It was just before his April phone call with Sam. Dean hadn’t been keeping close tabs, but he’d been paying enough attention to notice Cas hadn’t looked entirely put-together since around then.

Cas’s face hardens. He nods once. 

“Maybe you need a fresh perspective?” Dean tries, as the silence stretches on. “I’ve gotten stuck in ruts before, and it always helps to talk it out.”

Charlie and Jo are the best sounding board he’s ever had. Even better than Sam, since he could get a little preachy if he was too hungry or too tired, the giant baby.

“Maybe,” Cas admits. He throws Dean a long, considering look before saying, “The assignment involves another organization, and I’m having a hard time working with their representative.”

Dean groans sympathetically. “What’s wrong with them?”

“I… ” Cas drifts off, his expression troubled. “I’m not sure, but I don’t trust him. I don’t think I ever will.”

“Do you need to?”

Cas shakes his head. “I only need him to trust me in return.”

Dean grins, relieved. “Man, you got me worried it was something hard! That’s a piece of cake.”

“Is it?” Cas asks, a little incredulous and maybe a little offended.

Dean nods eagerly. “Getting people to trust you is all about give and take. You can’t put nothing in and expect to be best buds the next day.”

Cas’s brow furrows as he tries to puzzle through Dean’s advice. “But what exactly am I putting in?”

“Yourself,” Dean says with a shrug. “Share bits of yourself, and they’ll open right up.”

“That has not been my experience,” Cas says flatly.

Dean rolls his eyes. “Then you’re probably doing it wrong. Don’t give me that face - I have no idea how you’re fucking up - but if I had to guess, you’re probably overthinking it.” 

“Is that what you do,” Cas asks, staring at Dean with a laser focus, “when you have to get people to like you?”

Dean freezes. “Yeah, I guess so,” he says quietly, truthfully. “The more honest you are, the more natural you come across. Be yourself. Go with your instincts. They’ve worked out for you so far.”

“They have?”

“I’m here talking to you, aren’t I?” Dean says with a funny look. “There’s a reason I went on that date with you. And it’s not just because of your pretty face. I like you - rusty people skills and all. I’m not really into people who seem too good to be true ‘cause they always are.”

_“Oh.”_

“And, uh, speaking of our date,” Dean says hesitantly, “Do you wanna do something like that again?”

Cas tilts his head, confused. “I thought we had plans for this weekend? You said you were going to fix my car.”

Dean blinks at him stupidly for a moment. “I wasn’t sure we were still on. You never texted.”

“You never did either,” Cas points out.

“What?”

Cas pulls out his phone, squinting as the screen lights up. “I don’t think I ever heard from you after our date.”

Dean reddens. What a fucking rookie mistake. Communication misunderstandings were for amateurs.

After confirming his date with Cas, Dean feels like he’s walking on air the whole way to the firm. The barista behind the counter in the basement cafe where he gets Crowley’s morning cappuccino compliments him on his smile. He winks back at her, wishes her a good morning, and stuffs a five dollar bill in the tip jar.

She’s not the only one who notices.

“Someone’s looking better today.”

“Sorry?” Michael asks as he hands over Crowley’s morning coffee.

“You’ve been moping around here for the whole week,” Crowley says. “I thought your cat had died.”

“I don’t have a cat. I’m allergic,” Michael reminds him. He smiles. “But I didn’t think you cared.”

“I don’t,” Crowley mumbles, hiding behind his cup and drinking deeply. “But it doesn’t mean I don’t _notice_ things. I do have eyes, Smith.”

“Michael,” he corrects gently.

Crowley rolls his eyes. “Get me those copies of the Styne, Alastair, and Roman contracts from Dar. I have a meeting with Styne at noon sharp.”

“Yes, sir,” Michael demurs.

“And, remember, I’ll be taking Ramsay to a show in Beverly Hills tomorrow,” Crowley says. “I’ll send my driver to pick you up at three on Saturday to go over my final Q2 reports and Q3 forecasts.”

Dean’s heart drops to his feet. Shit, that was this _Saturday?_

“Uh, r-right,” Dean stutters. “Saturday, yes, I remember now.”

Crowley’s eyes narrow. Michael has never forgotten a single date or appointment in the past two and a half months. “What do you have happening that’s more important than our mid-year financials?”

“Nothing!” Dean protests. He has to get a fucking grip. Before he can stop himself, he tries desperately, “I - are you sure you want to do this at your house? We’ve worked at the office over the weekend before.”

“Yes, but Juliet won’t see me all Friday,” Crowley says. “And she gets anxious when she’s away from her papa.”

Dean holds back a face of disgust. At least Crowley didn’t call himself her daddy. 

Instead, he nods jerkily. “If that’s all, sir?”

“Yes, you may go,” Crowley dismisses him with a wave.

Dean flees. He bypasses his desk entirely and makes a beeline for the restroom instead. Safely locked in a stall, he pulls out his phone. He rereads the email Sam sent him, repeating the address in his head like a mantra.

Once he doesn’t feel like bashing his forehead against the mirror above the sink, he puts his phone back in his pocket and unlatches the stall.

Michael exits the bathroom ten minutes later, calm and composed.

**Notes for the Chapter:**

> We're really getting into it now! If you wanna chat, I'm on tumblr as [goldenraeofsun!](https://goldenraeofsun.tumblr.com/)


	4. The Rope

**Summary for the Chapter:**

> “So let me get this straight. We have three million dollars. What’re we gonna do? What do we want?” Jo runs a hand through her hair. “Better jobs?” she tries distastefully. “A pay raise? A fucking break?”
> 
> Dean clears his throat. “I want to stop. For good.”
> 
> Both heads swivel in his direction. Charlie nearly drops her hot pocket on the floor.

Dean spends his Saturday morning at the closest animal shelter to his apartment.

“I’m sorry, sir,” the receptionist says as Dean gets ready to leave, her face pinched with regret. “If you come back with a poster, we can put it up on our lost and found wall.”

Dean sniffs loudly and resists the urge to scratch at his watering eyes. “No, it’s fine,” he says in an unsteady voice. “I’m sure he’ll turn up sooner or later. Bob is such a dumbass, but I love the ginger idiot, you know?”

The receptionist nudges a box of tissues in his direction. “Don’t worry, I bet he’ll turn up soon. Cats are survivors, you know.”

Dean grabs a tissue for his runny nose. He blows noisily into it. “Thank you, really.”

“It’s no problem, Mr. Smith,” the receptionist says. She pats the back of his hand sympathetically. “Come back next week if you haven’t found him yet. We get new cats every day.”

Dean nods shakily and leaves with a tremulous wave.

For over an hour, he handled about half a dozen ginger cats. One or two even let him stick their faces in their fur as he mumbled something about them “smelling right.” The shelter volunteer showing him around hadn’t even batted an eye. Either cat people are _way_ weirder than Dean ever gave them credit for, or she was used to people going batshit over runaway pets.

Back at his apartment, he changes into his ratty sweatpants and a tee-shirt. He stuffs his pockets with wadded up tissues and rubs at his itchy eyes vigorously. 

Crowley’s driver texts him at 2:25 to say he’s outside.

Dean downs his allergy meds - they should take about twenty minutes to actually kick in - and heads downstairs.

Marco actually takes a step back when he catches sight of Dean.

“Mr. Smith?” he asks, making a face like he is hoping against hope he somehow got the address wrong.

“That’s me,” Dean says. He fakes a loud sneeze into his hands. Marco recoils. “Sorry, I was sleeping and didn’t hear you. I’ll be ready in ten minutes, I swear.”

“Uh.”

Dean lists to the side until he braces himself on the doorframe to stay upright. He squints at Marco. “You can wait, right? I know Mr. MacLeod doesn’t like tardiness.”

“No, he doesn’t,” Marco says slowly as he pulls his phone out. “I’ll call him to make sure.”

“Should I...?” Dean takes a step forward to take the phone, but Marco holds out a hand to stop him in his tracks.

“Yeah, boss? Yeah, I’m outside Smith’s place. He looks sick.” Marco shoots Dean a warning look not to come any closer. “Yeah, no idea what he’s got or if it’s contagious. He says he can still come over though.”

Dean sneezes loudly. And sneezes again.

Marco closes his eyes, his expression pinched. “Yeah, that was him. Do you want to talk?” Marco hands over his phone looking like he’d rather run over his mother than make skin-to-skin contact with Dean.

Dean coughs as he raises the phone to his ear. “Sir?” he says blearily.

“Marco tells me you’re under the weather,” Crowley says in an even voice.

“I’m fine. We have an,” Dean sniffs loudly, “appointment. I don’t miss my appointments.”

“Yeah, I think you’re going to have to miss this one, Mikey,” Crowley says sardonically.

“But sir-”

“No buts,” Crowley cuts him off. “I shook hands with about three dozen strangers yesterday at the show. I can’t risk falling ill now of all times.”

“Sir,” Dean says plaintively, still sniffling, “No, I can make it. It’s a 24-hour bug, I’m certain.” 

“Then I’ll see you bright and early on Monday,” Crowley says firmly. “Not a minute sooner.”

“Sir-”

“Rest up, Michael,” Crowley says, his tone almost gentle. “Eat soup, or something.”

He hangs up.

Dean hands the phone back to Marco, who gingerly stows it back in his jacket. “I guess you didn’t need to come after all.”

Marco throws him a dirty look before getting in his car and driving away.

Humming to himself, Dean heads back inside his apartment building.

* * *

Dean almost feels like himself by the time he pulls up in front of Cas’s small one-story bungalow. It’s in a nice neighborhood by the ocean Dean has never been to before - LA is freaking huge, after all. The nearby beach casts a briny tang to the air, and Dean makes a mental note to give Baby a thorough clean after this job. The corrosive salt can wreck her insides.

Cas’s affront to the automotive industry sits in his driveway, obnoxiously golden and impossible to miss.

Cas’s house is painted a pleasant if typical sea green color. Wicker outdoor furniture Dean would bet Cas never sits on is arranged on the wraparound porch. From Cas’s workaholic lifestyle, the house seems a little excessive. Dean would have pegged him for more austere apartment living, especially since Cas has told Dean multiple times he lives alone and would only host dinner parties on pain of death.

Cas answers the door with zero chill before the first ring fades. “Hello, Michael,” he says, a tad breathlessly. 

“Hey,” Dean says as Cas steps aside to let him in. “Nice place you got here.”

The door opens right into a living room with a couch, coffee table, and moderate flatscreen television. A bowl of brightly colored hard candies sits on the table, along with a closed laptop.

“Thank you,” Cas says. “Would you like anything to drink?”

Thank god. Alcohol. “Sure. Whaddya got?”

Cas leads him off to the kitchen on the left. A closed door on the right is probably Cas’s bedroom.

“I have beer, wine, lemonade, orange juice,” Cas lists, “and water, of course.”

“I’ll have a beer.”

Cas retrieves two bottles from the fridge and spends a minute rummaging around crowded drawers for an opener. “Sorry,” he mutters, “I don’t drink often.”

“No problem,” Dean says as he leans against the counter and studies the gleaming surfaces of Cas’s well-outfitted kitchen. Dean has never seen an oven with that many dials, and his refrigerator is twice as big as the one in Dean’s apartment. He counts at least five different knives in a wood block, which is only half the size of Jo’s collection, but still.

Bottle opener in hand, Cas opens their beers and hands one to Dean. “Cheers,” Dean offers.

“Cheers,” Cas intones solemnly.

Dean takes a sip. “How was the rest of your week? Everything work out OK with that other rep?”

Cas offers him a small smile, a barely-there quirk of the lips. “Yes, I believe so. Thank you for your help, I think it will be… invaluable.”

“Happy to be of service,” Dean says as he tosses Cas a two-fingered salute with the hand not holding his beer bottle. 

“And yourself?”

Dean grins. “Better, now I’m here. This place is a damn sight nicer than the inside of my office.”

Cas’s expression turns wry. “I know what you mean.”

“Please tell me you’re not riding the cubicle life, at least. It’s been breaking my heart to think of you stuck in some box moving decimals on a spreadsheet for twelve hours a day.”

Cas shakes his head. “No, I have a proper office. There’s even a window.”

Dean whistles. “Look at the numbers guy, living large.”

“It’s actually quite small,” Cas contradicts, “but it is suitable for my needs.”

“You’re not gunning for the corner office?”

“Not yet,” Cas says evenly. “I like my work now.”

“You do?” Dean asks, eyebrows raised. “It’s been running you ragged for two months.”

Cas inhales deeply. “Yes, it has, but it gives me purpose. It’s a challenge, and I like challenges.” He meets Dean’s dubious gaze, asking, “Do you?”

“Do I what?”

“Like to be challenged?”

Dean takes a long pull from his beer as he thinks over his answer. He can kind of wrap his head around where Cas is coming from, but all the recent challenges in Dean’s life had to do with figuring out stubborn marks, so Dean’s never exactly _relished_ it. After all, the reward of a job well done is the part Dean hates the most.

"Haven't known anything else, to be honest," Dean says, staring hard at the bottle in his hands.

Cas’s brow furrows, like he doesn’t really know what to say, but knows he should say something. Eventually, Cas settles on, “I’m sorry.”

“Don’t be.” It’s nothing Dean doesn’t deserve, at any rate. He’s the one who shit the bed before he knew the consequences. He was the moron who resorted to petty crime so CPS didn’t come knocking and take Sam away from him. 

And he was the same moron who got him and Sam separated a few years later anyway. Turns out, Lightbringer’s crew wasn’t too busy with the Moore job to notice the Winchesters skipping town. 

“Would you like to see the car?” Cas asks, breaking Dean out of his thoughts.

Dean hitches up an easygoing smile. “That’s why I’m here, right?”

As Cas breezes past him to the door, he says in a low voice, “I think we both know you’re here for more than the car.”

Cheeks red, Dean hurries to catch up.

* * *

After a drive in the Continental to hear the funny noise it makes when Cas accelerates, Dean gets down to business. He diagnoses the problem fairly quickly - a worn serpentine belt, which he was already 90% sure of based on the sound alone. He still deliberates under the opened hood of Cas’s car for a good twenty minutes to be extra confident he’s right. And if he bends over a little lower in his tightest jeans than he normally would, that’s what a real mechanic’s gotta do to get the job done. 

“Thank you so much,” Cas says as Dean closes the hood of the Continental.

“It's no problem.” Dean carries his toolbox - a souped up AAA emergency kit - back to the Impala. As he closes the trunk, he casts a searching look over at Cas, still by the Continental. “D’you wanna go for a drive in a real car?”

“My car is a real car,” Cas says as he rolls his eyes. Still, he gamely steps closer. “It has four wheels and takes me where I need to go. But if you insist-”

“I do.”

“-then I think I can be persuaded to take a ride in your car.”

Dean grins and opens the passenger-side door. “After you.”

Cas offers him a small if exasperated smile in return.

“Alright, Cas,” Dean says once they’re both in the car, “first rule of the Impala: driver picks the music and shotgun shuts his cakehole.”

“I understand.”

Dean says as he starts the engine. Baby purrs like a dream, like she knows how important this moment is for him. “Listen to that?”

“Yes, your car is very impressive,” Cas says, eyes crinkling.

Dean snorts at Cas’s clear attempt to placate him as they pull out into the street. “Where to?”

Cas glances around, his eyes a little wide at the prospect of making a decision. “You're the driver. This was all your idea.”

“Sure, but I've never been here before,” Dean argues as he steps on the gas.

“We could get dinner,” Cas suggests after an excruciatingly long pause. “What is your favorite food?”

“Pie.”

“That's not an appropriate dinner choice.”

“Shows what you know,” Dean scoffs. “I've had pie for breakfast, lunch, and dinner.”

Cas gapes at him. "Please don't tell me it was all in one day.”

“Yup,” Dean says, popping his lips on the 'p.'

It was right before his wedding - his very first one. Fresh faced, barely twenty, and nervous for all the wrong reasons. He was getting married to an equally young heiress named Lydia with a huge ceremony. Three hundred of Lydia’s closest friends, plus a dozen people to take up Dean’s side of the church: Sam, who was still allowed to work the same con as Dean, fake family members from their crew, and the Lightbringer himself, who always came to witness the Big Day.

Lydia was busy with family, so Dean had a whole chunk of time to contemplate his terrible life choices. When Sam asked Dean what he wanted to do, Dean sarcastically said all he wanted was to eat pie and watch Dr. Sexy.

Sam had immediately gone who knows where and gotten box sets of Dr. Sexy’s first seven seasons and three pies - pecan, apple, and cherry. And he ordered shepherd’s pie from room service, which wasn’t real pie, but Sam pouted and said Dean needed to eat something with vegetables.

Sam mocked the show relentlessly for _hours,_ but he stayed with Dean in his fancy hotel room above the wedding venue and made sure Dean didn’t dwell too hard on his Big Day ahead.

“You really enjoy pie that much?” Cas asks, skeptical.

Dean cracks a grin. “Fuck yeah. What about you? What’s your favorite food?”

“Burgers,” Cas says promptly. “They make me very happy.”

Dean laughs. 

“What?”

“Nothing,” Dean says with an easy grin. “But if I couldn’t have pie all day, it’d be a set of nice, juicy cheeseburgers. There’s this place, a shack off the coast of Delaware. The best fucking burgers I’ve ever had, man.”

Cas tilts his head, interested. “I’ve never been to Delaware.”

“I wouldn’t recommend it otherwise,” Dean says with a shrug. “Not much to do there except eat a fucking good burger.”

“What were you doing in Delaware?” Cas asks. “Turn here.”

“What?”

“Turn right,” Cas says, pointing. “There’s a diner about twenty minutes down this highway.”

Dean flips on his signal. “My dad had a job there when I was eleven, I think?”

“What did your father do?”

“This and that,” Dean says before Cas throws him a look for being vague. “He was a jack of all trades kind of guy. Some construction, some car repair, some minor plumbing or electrical if he could find someone to pay him off books ‘cause he wasn’t licensed for any of that crap.”

“And he could find enough of that work in Delaware?”

“God no,” Dean says with a dark laugh. “We moved a ton. I think I went to six high schools before I dropped out? I’m not really sure. How about you? Did you grow up with the white picket fence and block parties?”

Cas slowly shakes his head. “My family is very wealthy. I grew up on a large estate.”

Dean turns to him for a split second, eyes wide. “Shit, really?”

“Until I went to boarding school.”

Dean snorts. “You went to Hogwarts?”

Cas shakes his head. “It was an all-boys boarding school. We didn’t have Houses, and we certainly didn’t have magic classes.”

“That’s a goddamn shame.”

“Yes, I thought so too,” Cas says mildly. “Our exit is right up here.”

Dean switches lanes. “What was it like?” At Cas’s curious look, he elaborates, “Boarding school. Being shut up for months with a bunch of teenagers with the hormones and zits - sounds like a fucking nightmare.”

“They didn’t lock us in,” Cas says, smiling a little, but not like he’s really making fun of Dean. “I often went home on weekends. But otherwise, yes, it was pretty miserable. I am not very social by nature, and my classmates tended to be very insular and unwelcoming of anyone who didn't fit their idea of normal.”

“That sucks. I was a loner in high school too,” Dean says, glancing over at Cas. “Hazards of always being the new kid, I guess. Sammy hated it since he’s a big old softie. He always tried to make friends even though we were going to leave four, five months down the line. I always told him not to, but he never listened. Then he’d get his heart broken when we’d pack up and leave town.”

Cas’s expression turns contemplated as he says, “You reasoned it would be better to make no friends at all.”

“Well, yeah.” Dean throws him an odd look before turning back to the road. “Why bother starting something you know is going to end in tears?”

Cas hums thoughtfully. “Why indeed,” he murmurs.

* * *

“Thanks, sweetheart,” Dean says with a wink as he hands the menu back to their waitress. He turns back to Cas, who, surprise, surprise, is staring at him. “What?”

“Can you even turn it off?” Cas asks casually, but something dark lurks in his amused tone in his voice.

“Turn what off?”

Cas rolls his eyes. “The charm.”

“I - don’t...? Maybe?” he falters, feeling wrong-footed at the direct callout.

Cas chuckles under his breath. “I suppose it comes naturally to you.”

Dean’s gaze falls to his full water glass. He pulls it closer to keep his hands occupied. “I guess so,” he mumbles, his face heating. He can’t really say people gave a lot more free shit to a nice, likeable kid, over a normal, surly teenager.

“I always feel awkward around strangers,” Cas says.

“Have you always been like that?”

“Ever since I was a child,” Cas says ruefully. “I grew up in a large family.”

“Let me guess,” Dean says, leaning in, “You’re smack dab in the middle.”

Cas tilts his head, eyes narrowed. “How did you know?”

Dean licks his lips, saying, “You got that middle kid vibe going on - works extra hard ‘cause they always got lost in the shuffle, not used to attention. I would’ve thought you were the oldest, but your ambition isn’t the showy, controlling kind. And no way are you the baby of the family. Ergo, middle child.”

Cas blinks. “You’re very good at reading people.”

“One of my many skills,” Dean lies with a smirk. “So I’m right?” At Cas’s nod, he asks, “Do the rest of ‘em work in the family business too?”

“They’re all in different branches of the organization though, so we rarely interact.”

“Damn,” Dean says under his breath. He sits back. “I’d give anything to be able to work with my brother again.”

“In theater?” Cas asks, his disbelief clear in his tone.

Dean laughs and shakes his head. “Wouldn’t matter to me.”

“Do you miss him? When he’s on the road?” Cas asks.

“Every damn day.”

Cas’s intense eye-contact softens. “Were you close?”

“You could say that. Dad was in and out, so I had to look after Sammy, you know? He’s my kid brother. Someone had to make sure he went to bed on time and had clean clothes for school.”

“You were responsible for him,” Cas surmises.

Dean’s shoulders sag. He dropped the ball so far with Sam. “Yeah, I was,” he says, his voice barely audible.

“That’s very admirable,” Cas says, completely fucking clueless. Way to dig the knife in further. 

Dean takes a sip of water. What he wouldn’t give for anything stronger. 

“How is he?”

“Alright,” Dean says. “Worried about me, I think.”

“Why?”

Dean shrugs as he tries to come up with a way of spinning the truth. “He thinks I’m being reckless with my personal life ‘cause I don’t like my job.”

Cas shifts in his seat. After a beat he asks, “Are you?”

“Probably.”

They both look up as their waitress arrives, a bottle of ketchup wedged between her elbow and her body, hands full with two enormous plates of burgers and fries. “Here you go,” she says as she sets everything down. “Anything else I can help you with?”

“No, we’re all good, thanks Jamie,” Dean says, an involuntary smile on his lips.

The burger is halfway to his mouth when Cas asks, “Is it me?”

Reluctantly, Dean refrains from stuffing his face to ask, “Is what you?”

“The reckless element in your personal life,” Cas says evenly once he’s done chewing.

Dean frowns. “Kind of?” he tries. “He’d disapprove of anything that distracted me from the job.”

“Huh,” Cas says quietly, almost to himself. His expression turns adorably pensive. “Nobody has ever called me ‘reckless’ before.”

“Never?”

“I was a straight-A student in boarding school,” Cas says, his face deadpan. “The worst offenses I committed were a few late library returns.”

Dean shoves a few fries in his mouth. “And in college?”

Cas shrugs. “More of the same.”

“Where did you go?”

“Stanford.”

Dean sucks in a breath. “Sammy wanted to go there. Stanford was his top choice.”

God, what a fucking trip that would’ve been. If Dean hadn’t screwed the pooch, Sammy would’ve been a big-shot lawyer, and Dean would’ve been… Well, not lying to everyone around him and to himself.

“I didn’t know they had a reputable theater department.”

Dean bursts out laughing: Sam galumphing across the stage in period clothing, trying to sing Andrew Floyd Webber. “God no, he wanted to go to law school after.”

“Oh,” Cas says, taken aback. “He wanted to be a lawyer?”

Dean manages a nod. “He wanted to help kids - work with social workers and CPS and shit. I told him the system would chew him up and spit him out, but he thought he could make a difference from the inside.”

“And you?”

Dean pauses. “What about me?”

“What did you want to do?” Cas asks. “I assume you didn’t yearn to be a personal assistant.”

Dean takes a large bite and shrugs. “Didn’t give it much thought. I think I wanted to be a fireman when I was a little kid. Y’know, saving people.”

Cas studies him carefully. “You didn’t aspire to a particular field as you got older?”

Dean shakes his head. No time, looking after Sam, and then no opportunity, working for the Lightbringer. 

Cas squirts a symmetrical blob of ketchup near the edge of his plate. “It was always expected I’d go into the family business.”

“Did you want to?”

Cas swipes a few fries through the ketchup, ruining the neat circle. “A part of me,” he says quietly. “But the work is so demanding and often unfulfilling. I-” he glances up, almost guiltily, “I wanted to be an apiarist.”

Dean’s brow furrows. “What’s that?”

“A beekeeper,” Cas says, coloring slightly as he busies himself rearranging the bun so it sits perfectly atop the burger instead of listing off to the side. “Honey has fascinating properties, and the solitary life, out in the woods or on a farm… has always appealed to me.”

Dean snorts. “I can see why you settled in LA and work a nine to five in an office,” he says sarcastically.

Cas’s face falls. “Yes, well, I had a duty.”

Hurriedly, Dean reaches over to grasp his wrist, squeezing gently. “How about you and me take a trip to the Angeles National Forest sometime next weekend? It’d be a bit of a drive, but you could get your Thoreau on for a couple of hours.”

Cas smiles. “That sounds wonderful, Michael.”

Dean tries not to let his own smile falter at the name. “Awesome,” he says, his mouth dry. “It’s a date.”

* * *

The temperature has dropped as the hours have ticked on, but the incoming cold has nothing to do with the shivers coursing up Dean’s spine. He cuts the engine in front of Cas’s house. “So,” he says, turning to Cas. “What now?”

The glow from an overhead streetlamp across the street casts Cas’s profile in sharp relief, lit up from behind. He swallows. “I think that depends on you,” Cas says carefully. “I - would it be too forward to invite you inside?”

Dean reaches over to squeeze Cas’s hand. “Hell no,” he says seriously before he gets out of the car. Together, they hustle up to Cas’s house. Cas offers Dean a nervous smile over his shoulder as the key turns in the lock.

Cas is all over him the second the door closes behind them. 

Dean grunts, his hands automatically reaching up to grip Cas by the upper arms so they don't fall on their asses. He tries to get him to ease up, relax. 

Dean has nowhere to be, and, to the best of his knowledge, neither does Cas. Sure, he can appreciate a good quickie as much as the next guy, but they work best between ten in the morning and four in the afternoon, preferably in a company bathroom or in a locked office. Not after a leisurely drive and date in a 50s style diner just on the right side of Pleasantville. 

"Hold up, there, cowboy," Dean says, pulling back. "What's the-"

Cas cuts him off with a muffled groan of frustration. He surges forward, gluing their mouths together again. 

Dean breaks them apart again, this time with a barely bitten off curse. “Hey, come on,” he says, trying to inject a lightheartedness in his tone he absolutely doesn't feel. “Slow down.”

“Michael-”

The fake name sends an unpleasant trickling down his spine. Dean sighs, one hand pressed against Cas’s chest to keep him out of Dean’s personal space. He asks deliberately, “What’s the rush?”

Cas runs a hand through his hair, his blue eyes impossibly wide and frantic. “I…” he drifts off.

“Hey, man,” Dean says gently, “There’s no pressure here. It’s only me. We can do as much or as little as you want, but you gotta talk to me first.”

Cas swallows and meets Dean’s expectant gaze. “I need you here,” he says, his voice low.

“Alright, I’m here,” Dean says as he nudges Cas in the direction of the couch. This seems like a sitting kind of conversation. “And I’m not going anywhere.”

“Even if… we don’t…?”

“Nope,” Dean says easily. “If you just want to play Parcheesi until two am, that’s fine with me. I mean, I hope that’s not all we do _eventually_ ,” he adds quickly, “but that can be all we do tonight, okay?”

Cas sighs and buries his face in his hands. “I’m sorry.”

“Don’t be,” Dean says as he lays a hand on Cas’s shoulder and gives it a tentative squeeze. “It’s always good to talk things out. Especially if you’re feeling uncomfortable.”

Cas exhales a shaky breath as he lets his hands drop. “It’s been a long time.”

“Since you had sex?” 

Cas nods miserably. “Years.”

Dean’s jaw drops before he can rein his expression in. “But…”

Cas draws up short. “But what?” he asks, his tone defensive.

“But you’re all…” Dean throws Cas a disbelieving look.

Cas bristles. “I’m what?”

“Hot,” Dean says lamely. “If you wanted to find someone to sleep with, you can’t tell me there haven’t been willing dudes. Or ladies. I don’t know your preferences.”

“I am pansexual.”

Dean grimaces. Labels aren’t his thing. “My point still stands,” he says.

“Looks aren’t everything.”

“They are a big part of it,” Dean says frankly. “I once hooked up with a guy in the bathroom of a club. I don’t think we said two words to each other.”

Cas looks away. “I wish I had that advice. The last time I tried to ‘pick up’ a woman, I told her it wasn’t her fault her father ran off - it was because he hated his job at the post office.”

“What.”

Cas exhales a long sigh before he explains, his tone resigned, “She was my next-door neighbor growing up and I had run into her by accident in a bar.”

Dean tries to school his face into something not offensive. “Please tell me that wasn’t your opening line.”

“I introduced myself first.”

Dean makes a choked-off noise of laughter. “How the hell did you think that was a good idea?”

“In high school, I had heard it was weighing on her,” Cas protests over Dean’s snorts. “I thought she would appreciate some closure.”

Dean throws him an incredulous look. “I’m pretty sure she wanted to bury that shit where the sun don’t shine.”

“I gathered as much when she stormed out of the bar,” Cas says, a tad petulant.

Dean grins and claps his hands. “So what now? Parcheesi?”

* * *

They don’t end up playing board games. Instead, they… talk. Dean learns more bee facts than he knows what to do with and talks more about himself, his real self, than he has in years. Cas tells him a bit more about his family charity, but doesn’t bore him with too many accounting details.

Eventually, Cas gives Dean permission to buy a movie on demand for them to watch, and he chooses Star Wars Episode IV since Cas admits he has never seen it. 

They get halfway through Episode V before Dean falls asleep.

He wakes up on Cas’s couch, covered by a throw blanket and with his shoes off. He can hear Cas clattering around in the kitchen, and the sweet, sweet smell of coffee. 

“Mornin’ Cas,” he calls as he kicks off the blanket. “Sorry, I didn’t mean to doze off on you.”

Cas approaches, coffee cup in hand. “Hello, Michael.”

Dean eyes the cup speculatively. “That for me?”

Cas hands it over.

“You’re the fucking best,” Dean says before he downs half of it in one gulp. It’s warm, not too hot. Cas has been up for a while.

Before he can ask Cas about his plans for the morning, his phone rings.

“Fuck,” he mutters as Charlie’s name lights up the screen.

Cas hovers over him. “Is it an emergency?” he asks, brows drawn together in concern. 

“I hope not,” Dean says with a grimace as he takes the call. “Hey.”

_“It’s an emergency.”_

Dean groans.

“You gotta come to HQ, stat.”

“I’m busy,” Dean gripes as Cas walks back to the kitchen, out of earshot.

“With what? The porn can wait, Dean,” Charlie says, exasperated. “Get your ass over here. Jo’s found something huge.”

“What did she find?” Dean bends down to shove his boots back on his feet. “Don’t kill me with suspense, Charlie.” He adds in an undertone, “And don’t give me any bullshit about a secure line. _You_ set this line up.”

“Jo found three million underneath the floorboards of Crowley’s bathroom.”

Dean freezes. “What.”

“You heard me.”

Dean shoots a cursory look at Cas over his shoulder - his back is turned to Dean and he’s messing with something in the fridge. He curses under his breath. “I’ll be there in an hour.”

“Forget the porn!”

“I’m not watching porn!” Dean says, a tad too loudly. “I’m… not at home, alright?”

“Where the fuck are you?” Charlie demands at once. “You’re not at Crowley’s place.”

“I’m at a friend’s,” Dean says through gritted teeth.

“What friend?” Charlie scoffs. “All of your friends are in this apartment with me.” She pauses, listening. “Jo says get your ass over here too.”

“Yeah, yeah, keep your pants on,” Dean mumbles as he looks around for his coat. “I’m on my way over.”

“Good,” Charlie says, “See you soon.” She hangs up without waiting for him to respond.

Dean’s heart sinks as he stands up and turns around. “Cas?”

“Yes?” Cas turns, both hands holding two bowls of cereal. “I hadn’t put the milk in yet,” he says, glancing down. “It gets soggy if I pour it in too early.”

“Listen, man,” Dean says, striding forward, his face contrite. “I gotta go.”

Cas blinks. “Oh.”

Dean scrubs a hand down his face. “I’m sorry.”

Cas sets the bowls down. “It’s fine.”

“I’m sorry,” he repeats.

“I can put the cereal back,” Cas says, turning his back to Dean as he reaches for the box.

Dean feels like the shittiest heel on the planet. “Look, I’ll call this time, alright?”

Cas nods once. “I hope so.”

“Hey.” Dean steps closer. He grabs Cas’s hand and squeezes. “I had a really good time last night,” he says. “I want to do it again, okay? Something just came up.”

“Okay.”

Dean throws caution to the wind and leans in to press a lingering kiss to Cas’s mouth. His lips are warm and dry and taste like too-sweet coffee. Dean swipes his tongue against the seam of Cas’s mouth, and Cas’s lips part with a tiny sigh. He cups Cas’s face with his hand, one finger tracing that incredible jawline, raspy with stubble.

“I’ll see you soon, okay?” Dean murmurs after he pulls away. “Let me know if you can’t show on Monday at the usual place.”

“Yes, Michael.”

Dean throws him a strained smile before seeing himself out.

* * *

“Three million.”

“Almost four,” Jo sighs as she flops down on the couch next to Dean.

Dean glances over at Charlie, for once not hiding behind her computer screens. She’s standing at the counter of the open kitchen, glaring at a hot pocket spinning around in the microwave like it personally ordered a hit on her parents. “Have you told him?”

“The Lightbringer?”

“No, the fucking Kool Aid Man,” Dean scoffs. “Of course the Lighbringer.”

Charlie crosses her arms across her chest. She huffs, “No, not yet.”

Dean narrows his eyes. “Why?”

“Because Jo sent me the news at eleven last night, and I don’t want to interrupt Lilith’s beauty sleep?” Charlie snarks.

Dean holds up his hands in a gesture of surrender. “I’m just asking.”

The microwave dings and Charlie immediately darts her hand in to fetch her prize. Swearing at the heat, she drops it on a waiting plate and turns back to face them. “I wanted to consult with you two first. You know, my _team.”_

“Ain’t that mighty nice of you,” Jo drawls. 

Charlie sighs as she walks into the living room. “Look - I thought this is something we could use. You know, leverage as a unit.”

Dean eyes her hot pocket with undisguised lust. Still, he says, “Gee, I don’t think the Lighbringer recognizes labor unions or collective bargaining.”

“We’re his most valuable team,” Charlie says in a deadly serious voice. She fans her plate with her hand. “I think he’ll listen to us.”

Jo sits up a little straighter. “We are? How do you know that?”

Charlie shrugs. “Hacked his servers. Took a peek at the financials.”

“You can do that?”

“What, like it’s hard?” Charlie quips.

Jo laughs. “I’m guessing nobody caught you.”

“My head is still attached to my neck, so no, they did not,” Charlie says.

“What else did you find?”

“Potential marks. Past jobs. Where he’s keeping your mom,” she says, tipping her head at Jo, who pales. “Where Sam’s gonna be sent over the next year,” she says, sharing a significant look at Dean. She clears her throat. “I can’t get it all, though. They’re set up like the Mob - or the Catholic Church - a strict hierarchy. I only got access through one branch - the western division. The rest are totally separate from ours and completely encrypted on separate servers.”

Both Jo and Dean are silent.

Jo runs a hand through her hair. “What’re we gonna do? What do we want?”

_To get out._

But Dean keeps his mouth shut. To say it would make it real, turn the pipe dream into a cold hard reality - with stakes, and risks, and who knows what else. Jo and Charlie are his best friends, but Sam is _family._ And if Dean does anything to jeopardize him again, he could never live with himself.

“Better jobs?” Jo tries distastefully. “A pay raise? A fucking break?”

Dean stares at his hands.

“When did you find all this shit out?” Jo asks Charlie. “You must’ve pulled an all nighter for that intel.”

Charlie swallows. She looks down, tapping at her hot pocket with nervous fingers to test the temperature. “Two years ago, maybe a little more.”

Jo lurches to her feet, demanding, “And you didn’t think to tell us until now?”

Charlie cringes. “I didn’t think it would matter!”

“And now it does?” Jo hisses, nearly shaking with anger. _“Why?”_

“Because I didn’t know you then!” Charlie says, her voice going shrill. “Why the hell was I gonna tell you I had the keys to the kingdom? For all I knew, you’d turn right back around and report me! I’ve been run out of town before - and I _hate_ starting over.”

“Nuh-uh,” Jo says, her eyes flinty. “I don’t buy it. We start over every ten months anyway. That’s what we _do.”_

“But it’s a team effort,” Charlie mumbles. “It’s different when you’re on your own.”

Jo sits back down. Eyes still narrowed, she says, “You’re really hung up on this team thing, aren’t you?”

Charlie shrugs. “I’ve always been a loner. Never really fit in anywhere. And then I got friends. It’s been... nice.”

Jo rounds on Dean. “You’ve been awful quiet over there. What gives?”

Dean shakes his head. “Just thinkin’.”

“Don’t hurt yourself.”

Dean kicks her foot. “Shut up.”

Charlie nibbles on the edge of her hot pocket. “What _are_ you thinking, Dean?”

“Nothing.”

“I don’t believe that for a minute,” Jo says scornfully. “What do you want out of this? More time with Sam?”

Dean shakes his head, actually listens to Jo’s words, and nods.

“Aren’t you helpful,” Jo says dryly. She turns back to Charlie. “What’s the Lightbringer got on you, anyway? My mom, his kid brother.” She jerks her head in Dean’s direction.

“Nothing.”

“Seriously?”

Charlie takes a big bite of her hot pocket. With her mouth full, she explains, “He caught me stealing from hedge funds and shady super-PACs. Mostly giving to my fave charities and stuff, but also skimming from the top. I was living comfortably, and the Lightbringer said I could live… more comfortably.”

“You’ve got to be shitting me,” Jo says, her mouth falling open. “He’s really got nothing on you?”

“Nope.” Charlie grins. “At least, nothing that can’t be shoved into a cyber black hole.”

Jo frowns. “I thought nothing on the internet gets really deleted.”

Charlie says with a grins, “Not if you’re me.”

Dean clears his throat. “I want to stop. For good.”

Both heads swivel in his direction. Charlie nearly drops her hot pocket on the floor.

* * *

Dean returns into his apartment around midnight, entirely strung out from his full day at Charlie and Jo’s. The oily Chinese food they ordered for dinner hours ago nearly turns his stomach, or it might be nerves now he actually sees a light at the end of the tunnel.

He undresses and brushes his teeth by rote memory. In bed, he stares up at the ceiling, his mind spinning. 

Jo and Charlie will take off with two million and fetch Ellen. Dean will take the rest, meet up with Sam, and the five of them will reconvene at Sam’s safehouse in Sioux Falls. After that, the plan gets hazy. They could split up, make it harder for the Lightbringer to find them all - or they could stick together and use their combined talents to stay off the radar.

Hard to believe this time last night he was explaining to Cas why it was so important Han shot first.

Dean turns over in bed and grabs his phone, lying innocently on his nightstand. He wakes up the screen with a few impatient taps of his index finger.

He closes the email outlining the plan they sent to Sam earlier that day, and pulls up his messaging app. Fuck this. If he has limited time left in LA, he’s going to spend it with Cas.

 _Dean 12:31  
_ _You still up?_

He rereads his text, sent with no way to unsend it. Dean groans silently. His text reads like a horny, lonely jackass with nobody to fuck. Of course Cas probably isn’t still up. He’s an adult with an important job tomorrow.

 _12:31  
_ _Yes_

Dean’s heart soars.

 _Dean 12:31  
_ _Dude why_

 _12:31  
_ _I don’t sleep much._

 _Dean 12:31  
_ _By choice?_

 _12:31  
_ _It’s partially my choice and partially my biology.  
_ _It helped me a great deal in university and in getting my latest promotion._

 _12:32  
_ _Why are you still awake?_

 _Dean 12:32  
_ _Can’t sleep._

 _12:32  
_ _By choice?_

 _Dean 12:32  
_ _Got too much to think about_

 _12:32  
_ _Like what?_

Dean groans to himself. He shuts his eyes, but he can still see the afterimage of the screen, superimposed on his retinas. Traffic churns by outside at a slow pace, and a horn blares somewhere down the street.

 _Dean 12:33_ _  
_ _Plans for the future_

Cas doesn’t immediately text back, and Dean focuses on breathing in and out at a steady pace to calm his racing heart.

 _12:35_ _  
_ _Do you mean next weekend?_

Not exactly.

 _Dean 12:35_ _  
_ _yeah_

 _12:36_ _  
_ _Would you like to stop by around 10:30? Is that too early?_ _  
_ _I figured you would like to drive us there :)_

Dean chuckles at the emoticon. Who knew that serious exterior was hiding such a secret dork.

 _Dean 12:36_ _  
_ _Sounds great._ _  
_ _I’ll bring food too. Any allergies?_

 _12:36_ _  
_ _No._

 _Dean 12:36_ _  
_ _Awesome. I’ll grab cold cuts and stuff for sandwiches. OK?_

 _12:36_ _  
_ _I have been known to eat a sandwich or two._

 _Dean 12:36_ _  
_ _Duh, I’d hope so. Or else I’d think you were a robot or something._

 _12:37_ _  
_ _I am not a robot._

 _Dean 12:37_ _  
_ _Yeah, buddy, you passed the test. 4 for u, Glen Coco_

 _12:37_ _  
_ _That seems like a reference._ _  
_ _I don’t understand that reference._

 _Dean 12:37_ _  
_ _Remind me to put Mean Girls on next time we have a night in_

 _12:37_ _  
_ _Of course :)_

 _Dean 12:37_ _  
_ _I’d better turn in. Full day of work tomorrow._

 _12:38_ _  
_ _Sleep well. I’ll see you in the morning._

 _Dean 12:38_ _  
_ _:)_

* * *

“Michael!” Crowley’s eyes widen as he takes in the man before him, complete with his usual morning coffee order. “Glad you see you up and about. You sounded awful on the phone.”

“I’m sorry, sir,” Michael demurs. “It came out of nowhere.”

“Let’s hope that’s the case,” Crowley says, shuddering, “and something isn’t going around the firm.”

“I’ll keep a lookout, sir,” Michael says with a small smile.

“Now,” Crowley says as he taps something on his computer and turns to give Michael his full attention. “We never did have that chance to go over reports on Saturday since you came down with the plague.”

“How about a long lunch today?” Michael proposes. “You have meetings until eleven thirty, but nothing until four in the afternoon. I could reschedule that - Cecily would understand.”

“Yes, she would,” Crowley muses, almost to himself. He looks up at Michael, still standing over his desk. “Have you ever been to Inferno?”

It’s Crowley’s favorite date restaurant. A fancy, pretentious place with eye candy waitstaff the manager bribes into working for her with promises of Hollywood connections.

“I can’t say I have,” Michael says slowly. “Should I make reservations?”

“No need,” Crowley says, waving his hand in dismissal of the very idea. “They’re never too busy to seat me.”

Michael nods and straightens. “If that’s all?”

“Postpone that meeting with Cecily for tomorrow,” Crowley says, his attention already turning back to his computer screen. “That will be all.”

Michael ducks out of Crowley’s office with a quiet, “Yes, sir.”

Back at this desk, Michael wakes up his computer. He checks his email, reluctantly accepts an invitation to yet another happy hour with the other assistants, and gets started on creating his to-do list for the day to share with Charlie, still playing remote backup assistant at the apartment.

He’s only halfway through dealing with a crisis with the Roman account when Charlie pings him with a new message on their private chat that wipes itself clean at the end of each business day.

 _Queen_ _  
_ _You never said where the hell you were Sunday morning. The GPS on your phone was off. What gives?_

Dean grimaces at his screen. Fingers pausing on the keyboard, he surreptitiously glances over his shoulder. The door to Crowley’s office is closed, and the rest of the assistants all appear to be focusing on their own shit.

 _Handmaiden_ _  
_ _Have you been spying on me?_

 _Queen_ _  
_ _You're surprised?_

 _Handmaiden_ _  
_ _Not now_

 _Queen_ _  
_ _Yes now. If any of this is going to work, you can’t keep things from us._

Dean grits his teeth as he reads over Charlie’s latest message. If anyone can force it out of him, it’s Charlie. All three of them could give each other a run for their money in the stubborn jackass department, to be honest, but Charlie’s got the brains on her side. Dean can persuade a fish to buy desert real estate, but he's always shit out of luck whenever he tries to convince Charlie of anything. 

_Handmaiden_ _  
_ _I’ll tell you later._

 _Queen_ _  
_ _Dammit - I’m getting worried. Tell me or I’m going to pull you out of work and let Jo work you over instead._ _  
_ _I’m talking full on Spanish Inquisition._

 _Handmaiden_ _  
_ _Fuck you. I’ll call in five. I’m not typing this shit out._

Dean scrubs a hand down his face, gathering himself together before he books it to the handicapped restroom at the other end of the hallway. He locks the door, inhales a fortifying breath, and dials Charlie's number. 

“Spill, Winchester.”

Dean turns away from his reflection in the mirror. “His name is Cas.”

“Is he your new bestie?”

Dean rubs at the back of his neck. “I’m kind of seeing him.”

 _“ You ’re what?”_ Charlie shrieks. 

Dean yanks the phone away from his ear. “Jesus, calm down!”

“I’l calm down once I recover from my heart attack!”

Dean sighs. “Look, it's not serious.”

“Oh yeah?” Charlie demands. “If it’s not serious why were you hiding him? Why were you risking the con for him? _Why would you even consider it?”_

Dean shakes his head. “I don’t know.”

“Bullshit,” Charlie declares. “I can't believe you’re so selfish, Dean.”

“Selfish?” Dean echoes, outraged. “I never do _anything_ for myself. My own fucking body isn’t mine half the time - so give me a _fucking break.”_

Charlie is quiet on the other end of the line for a long while. “Is this going to change our plans?”

“No.”

She presses, “Are you sure?”

“Yes, I’m fucking sure,” Dean says gruffly. “Are you?” he asks, and it only occurs to him once the words are out of his mouth that they make no sense.

But Charlie responds, "The Lightbringer has my mom too.”

Dean freezes. “What?”

“They were in a car accident when I was twelve. It was my fault. My dad died, but Mom survived. She’s been in a coma ever since. The Lightbringer found the best doctors for her, and the best facility for treatment.” Charlie’s breath hitches, the only pause in her word vomit. “But she’s gone. She hasn't been my mom for a long time.”

“Charlie…”

“I thought, if we got the momentum going I wouldn't have to think about it. I could finally let her go.”

Dean swallows down his lingering anger. He says, as gently as he can manage, “If you ignore it, that’s not the same as accepting it.”

Charlie sniffles. “It feels like I’m killing her all over again.”

“You’re not.”

Charlie exhales a wet sigh. “About this guy - Cas.”

“Yeah?” Dean asks warily. 

“Is he going to be a problem when we leave town? I get that you’re not. But is he?”

Dean squeezes his eyes shut. “No,” he murmurs. 

“Are you sure?”

Dean lightly bangs his fist against the side of the sink. “We’ve only been on two dates. We haven’t even slept together.” He doesn't tack on the _yet_ he wants to say so badly his chest aches.

“Sex isn’t everything.”

“It’s not serious,” Dean repeats, even though this thing with Cas is the most serious relationship he’s had since he was sixteen. But Dean’s worse than emotionally constipated when it comes to real feelings; he just plays them on TV.

“Kind of sounds serious.”

“I haven’t told you anything about him.”

“What’s his last name?”

“So you can stalk him?”

“Do you think he won’t pass my tests?” Charlie challenges. 

“Stevens.”

“Cas Stevens?” Charlie asks in a funny voice. “Weird name. Give me a couple of hours.”

“You don’t have to do this,” Dean tries, a last ditch effort. But deep down, he can acknowledge she’s only looking out for them - his own investigation into Cas was cursory at best. Still, a part of him needs to keep Cas a secret, something entirely his. 

“I really do,” Charlie says before she hangs up on him.

* * *

Jo calls the moment Dean steps foot into his apartment after his long fucking day because Dean can’t catch a break.

“What?” he answers. “I just got home from making out in the bathroom of a five-star restaurant with Crowley. I need to bleach my mouth. Can it wait?”

“You weren’t gonna tell us your big plan was all because of _a boy?”_

Dean sighs. “What the fuck are you talking about, Joanna Beth?”

He puts her on speaker and drops his phone on the bed as he strips out of Michael’s suit.

“I’m talking about how we’re risking our lives because of _a boy.”_

“Can you stop saying it like that?” Dean says as he kicks off his pants. “He’s a fully grown man.”

“Sure he is.”

“Ask Charlie.”

“I will,” Jo says, “As soon as she gets a read on him.”

“She hasn’t yet?” Dean asks, surprised.

“Nope,” Jo says, her voice suspiciously cheerful. 

Dean’s stomach lurches. Charlie _always_ finds the skeleton in the closet. The longer it takes, the worse they are. “Fuck.”

“Serves you right. I can’t believe you kept this from us.”

“Can it. Charlie already read me the riot act.”

“I hope Sam did too.”

“He didn’t exactly approve when I told him.”

Jo sighs. “You’re not going to pull a fast one on us again and do something incredibly stupid like take him with us, are you?”

Dean’s eyes nearly bug out of his head. His fingers slip undoing the next button on his shirt. “What?” 

“I said-”

“I heard what you said,” Dean interrupts. “And no, I’m not going to drag him along, Jesus.”

“Are you sure?”

“One, we’ve been on _two fucking dates_. This isn’t some torrid romance or whatever you’re picturing.” Dean finally wrests himself out of his shirt. “B, there’s no fucking way he would agree - so I’m not going to ask. Quit your worrying.”

“Good,” Jo says firmly. “I have reservations enough about this whole plan as it is. I don’t need a fifth element in the mix to think about.”

“How are we on getting the cash out of Crowley’s place?” Dean asks.

“We’re working on it,” Jo says. “Do you want to keep him occupied with a romantic weekend getaway?”

“No.”

“Tough nuts.”

Dean sighs. “This weekend?”

“If possible.”

“I don’t know if he’d go for it on such short notice,” Dean tries as he picks his phone up and places it next to his ear.

“So make Michael the type to work fast. You’ve spun it before.”

Dean sits down heavily on his bed. “I already have plans.”

“Cancel them.”

Dean exhales a slow breath. “I’ll let you know.”

“Dean,” Jo starts, her tone kind, “You should really think about it - if you’re going to pack up and leave town, maybe now’s the time to start pulling away. It’s the nice thing to do. For his sake.”

Dean blinks hard, a heavy weight settling behind his breastbone. He leans forward, bracing his elbows on his knees. “I know,” he says quietly into the receiver.

“Just a thought,” Jo says. “For what it’s worth, I’m sorry.”

Dean hangs up on her.

* * *

Dean doesn’t cancel his plans with Cas. He moves them to the weekend after next instead. He blames the raincheck on work and the weather since it’s supposed to pour all Saturday. Cas doesn't question him and says he needs to catch up on work anyway. 

On Monday, as Michael hands over Crowley’s morning coffee, he brings up a voucher he received for a weekend at a bed and breakfast near Santa Barbara. It’s not wine country, but there are a number of promising vineyards in the area. Luckily, according to their research, Crowley isn’t as much of a wine snob as he is about whiskey. Michael tells Crowley he’s going with a couple of friends.

Tuesday evening, Michael tells Crowley his friends made other plans by accident, and asks Crowley to come along instead. Crowley hems and haws, refusing to give a concrete yes or no. As obliging as ever, Michael says he doesn’t need an answer until Thursday.

All day Wednesday, Michael sends Crowley lingering looks whenever he passes by his office and dawdles while dropping off his afternoon coffee. He and Charlie successfully get a first strike levelled against another senior partner, Eve. Two more, and she will follow Abbadon out the door. 

On Thursday morning, Michael gets his yes.

Dean skips his usual trip to Hallowed Grounds on Friday morning. He can’t face Cas with a weekend full of Crowley looming over him.

Instead, he packs his overnight bag: two changes of clothes, his cell phone charger, toiletries, a small bottle of lube, and condoms. He slips a few roofies from the unmarked bottle in his medicine cabinet into his wallet.

In the office, Michael beams as he deposits the cappuccino on Crowley’s desk. “Good morning, sir.”

“Is it?” Crowley asks dryly. 

A little offended, Michael says, “It’s Friday.”

“I hear ‘TGIF’ come out of your mouth,” Crowley says calmly, “I will sack you right here and now.”

Michael smiles, mood undeterred by the idle threat. “I was going to say I was looking forward to our weekend together, sir.”

Crowley ducks his head to mark something down on a sheet in front of him. He says, flustered, “Of course you are.” He shuffles his papers around and looks back up. “I hope this _bed and breakfast_ ,” he says the words like anyone else would say ‘flea-ridden hovel’, “of yours is up to my standards. I have a minimum thread count, Michael.”

Michael chuckles. “I packed a spare set of sheets if they’re not up to par.”

“You have a spare set of Egyptian cotton in your linen closet?” Crowley asks sardonically.

Michael bites his lip. “I can pick some up on the way.”

Crowley rolls his eyes. “I suppose I can bear it for one night - for you, mind. I wouldn’t do this for just anybody.”

“Of course not, sir,” Michael says, a smile playing on his lips.

* * *

Dean slips out of the room and closes the door quietly behind him. He can’t wake up Crowley, whistle-snoring away on the bed. The roofies Dean slipped into his wine at dinner should render him unconscious for six to eight hours, but marks have woken up early before. The scene is all set up for _the morning after;_ a trail of Michael’s clothes from the entrance to the bed; an overturned bottle of lube on the nightstand; pillows knocked to the floor. 

The bed and breakfast is dark and quiet at this hour. Most guests are probably sleeping off too much alcohol - the hazards of being rained in at a vineyard. Dean slips down the stairs to the first floor, bypassing the empty dining room and waiting area by the entrance. He opens the door and shivers a little at the cool breeze and pungent smell of rain.

It’s still pouring buckets, so Dean sticks to the porch. He leans against one of the posts, breathing quietly to himself.

The night went without a hitch - Michael and Crowley got good and drunk at dinner. Michael made his move just before the drugs kicked in, and they barely got to more than handsy making out before Crowley started to flag. 

It was technically a success, but Dean can’t muster a smidge of satisfaction. The whole time he thought of Cas. Every forced, fake smile sent him spinning back to Cas.

But Dean is not an idiot. Cas will never see him again after this week.

Dean drags the least-damp outdoor chair back towards the wall, out of the way of splattering raindrops, and falls into it.

What would Cas say if Dean asked him to drop everything, run away with a man he’s barely known three months, and live among criminals?

Nothing good.

He tries to picture Cas’s face - offended Dean would suggest something so stupid? Disgusted with Dean’s clinginess? Angry that Dean would presume he’s more important than anything else in Cas’s life? 

But deep down, Dean knows Cas would simply be surprised. He would look at Dean with those expressive blue eyes, all sad and pitying and shit, and tell him in a nice but detached way that Dean isn’t worth it.

Dean gets it. He’s been lying to Cas since Day One. He might forget the thousand lies that brought him to Cas’s figurative doorstep when they’re together, but the fact remains: if Cas knew what Dean was, he’d run as fast as he could in the other direction. Cas is a smart guy, after all. Dean is a dumbass to even consider asking Cas to stay with him.

It’d be better for Dean to leave. A clean break before anything real can put down roots.

Dean groans aloud and buries his head in his hands. 

He pulls out his phone, wincing as the bright light of the screen sears his eyeballs. His finger hovers over Cas’s unnamed contact, tantalizing in its closeness. One slip of his thumb, and he could be talking to Cas right now.

Or, most likely, he’d get Cas’s voicemail because it’s two-thirty in the fucking morning. 

Dean nearly hangs up five times as the phone rings and rings.

“I don’t understand. Why-why do you want me to say my name?”

Dean laughs out loud from Cas’s ridiculous recording and maybe a little at the sound of his voice.

“Hey, Cas,” Dean starts. “Sorry for calling so late. I guess you must be asleep. I just…” he drifts off, unable to fucking say it. “I just wanted to say I don’t think I’ll be able to make our date next weekend.” He swallows around the lump forming in his throat. “Sorry for cancelling, man. I know you were looking forward to it. I was too.” 

He waits a beat, inhaling deeply to gather himself. “And our standing coffee date - I’m gonna have to bail on you for those too. I don’t want to, _believe me._ ” He stares out at nothing. The vineyard lies a couple yards beyond the porch railing, but Dean can’t see five feet in front of his face in the rain. 

“You’ll never see me again,” Dean says hollowly, “the sooner you accept that, the better off you’ll-” He cuts himself off, disgusted at falling into the same goodbye speech he always gives his marks. “Fuck, Cas,” he swears quietly. “All you gotta know is seeing you was the best part of my morning. It’s important to me that you know that. Okay, well, bye.”

* * *

Crowley is surprisingly malleable the next morning. He accepts Michael’s story of the night before without much argument and seems keen on doing it again. When Michael says he’s too sore for a morning quickie, Crowley doesn’t push. 

The storm cleared sometime before dawn, so they can leave the B&B and shake off the cabin fever making Michael antsy and distracted. Michael opts to go to the first tasting of the day, so by half-past ten, he’s already buzzed.

By mid-afternoon, Michael begs off for a nap. All the wine made him sleepy. They lie together on the bed, Michael curled up in a comma shape, his back against Crowley’s side, and Crowley sitting up with his laptop to get some work done.

When Michael wakes up before dinner, he claims he’s too hungover and hungry for more than a few kisses. Instead of eating at the BnB, Crowley surprises Michael with a quick ride to a nearby English pub, saying, “If I forgo the five-star treatment, I might as well do it right. And there’s nothing like pub food for a hangover.”

Crowley sticks with a classic shepherd’s pie and laughs at the face Michael makes as he tries mushy peas for the first time.

They only briefly stop back at the bed and breakfast to pack up their things and check out. By seven PM, they’re on the road, back to LA. 

Michael gets carsick, though, through some combination of the alcohol from earlier and a heavy dinner. He spends most of the ride looking out the window, his face slightly queasy. Crowley, never one to shy away from the sound of his own voice, keeps up a one-sided conversation for most of the two-hour drive. Michael makes a noticeable effort to perk up as they pass the city limits.

He turns to Crowley as he double-parks the car outside his apartment building. “Thank you for coming with me this weekend,” he says, his voice hushed.

Crowley leans forward. “It was my pleasure, Michael.”

Michael licks his lips. “I’ll see you tomorrow, then?”

“Tomorrow,” Crowley murmurs, “or we could-” He closes the distance between them without finishing his sentence. 

But Michael breaks their kiss before too long. “We’d better not,” he says ruefully. “You have a meeting with Styne at eight, and god knows if I wake up with you again, I won’t let you out of my sight until at least noon.”

Crowley blinks dopily at Michael for a long moment. “Right, well, we can’t have that,” he says gruffly. “Out you go.”

Michael reaches over and squeezes Crowley’s hand before getting out of the car.

Dean watches Crowley drive off. This was it; his last night in LA and his last night working for the Lightbringer if everything goes to plan. 

He should be happier.

He unlocks his apartment and drops his overnight bag by the door - no use unpacking it when all he has to do is gather the rest of his shit up. First things first, though. He pulls his phone out and dials Charlie’s number.

“You got the payload?” he asks without waiting for introductions. He puts her on speaker and drops his phone on the bed as he rifles through his chest of drawers for anything of sentimental value. All of Michael’s suits can go fuck themselves.

“Yeah,” Charlie says. “Are you on your way over?”

“Gotta pack first,” Dean grunts as he pulls out a few tees and a couple of essential pairs of jeans. He can’t go on the run pantsless.

“Pack fast. Our ETD is in forty. Especially if you want to stow your car somewhere safe.”

“My baby comes first.”

“Uh huh.” Dean can hear the eye-roll in her voice. “I love my computer, but I’m not hauling fifty pounds of equipment halfway across the country.”

“That’s ‘cause it’s not real love.”

“Bite me, Dean.”

“You first,” Dean snarks back without any heat. He clears out his underwear and sock drawers.

“You know I don’t swing that way,” Charlie is saying.

Dean laughs. “Thank god for that.” He darts to his bathroom before remembering all his toiletries are already in his overnight bag.

“I’ll see you in ten, Charlie. Traffic looked light on the way in.”

“Good.” She hangs up.

Dean stuffs the small pile of clothes into his suitcase, retrieves his emergency cash from the bottom of a vase of fake flowers and is almost at the door when the doorbell rings.

He checks his phone in his hand like there’s any reason on Earth Charlie and Jo would come to him instead of meeting at their place, per the plan. The screen stays confusingly blank.

Warily, he peers through the peephole to see a familiar shock of dark hair and blue eyes squinting at the peephole like he knows Dean is already on the other end.

Dean opens the door. “How did you know where I-” he starts, his words breaking off as Cas fumbles in his coat pocket.

“Hello, Dean,” Cas says as he holds up a laminated badge. “We need to talk.”

The floor drops out from beneath Dean’s feet.

**Notes for the Chapter:**

> Next chapter up on Wednesday!


	5. The Tale

**Summary for the Chapter:**

> “Don't I get a phone call?” Dean hollers. He must’ve been stuck in this interrogation room for hours, mostly alone.
> 
> They first tried to get some junior agent to work him over, but Dean stayed stubbornly uncooperative. At the start, he probably should have tried to butter the agent up, but Dean was still so pissed off about Cas he blurted the first thing that came to mind: “Did you take a wrong turn on your way to your boy scout troop?”
> 
> Agent Alfred “I Can’t Grow a Beard” Samandriel didn’t stay long. 

Dean feels like Wile E. Coyote after he’s run headlong into a solid brick wall. Pained and confused, Dean stares at the badge in Cas’s hand, upside down, but “FBI” is hardly impossible to read, even if it’s the wrong way up.

“May I come inside?” Cas asks in an undertone.

Dean doesn’t budge an inch. “Why?”

“Because I don’t want to have the conversation in your hallway,” Cas says, sparing a fleeting glance at the rows of closed doors to his left and right.

“I think the hallway is a perfectly good place to have it,” Dean argues stupidly.

Cas’s jaw clenches. “I am armed.”

“Good for you,” Dean says with forced cheer. “But if you’re looking to keep this quiet, shooting me in the doorway of my apartment isn’t the way to do it, buddy.”

“It was a warning for you not to run,” Cas says with a pointed look at the bags still in Dean’s hands. And yeah, running seems like such a good idea right about now. “Will you let me in or not?”

“How about no?” Dean tries. 

Cas throws him a hard look before roughly shouldering past him. He closes the door behind him and turns to face Dean. He stands uncomfortably close, and _fuck,_ Dean is so not prepared for any of this.

“We need to talk about the Lightbringer.”

“You know about the Lightbringer?”

Cas nods jerkily. “I do.”

Dean bends down to stack his bags one on top of the other by the door. He hasn’t ruled out making a break for it, but Cas _could_ shoot him at any moment, so he’s demoting that one to Plan B. He crosses his arms over his chest. “Why should I tell you anything?”

Cas’s mouth thins into a hard line. “If you don’t tell me, you’ll be telling my superiors. They are only a phone call away and fully ready to bring you in.”

Dean swallows, fighting to keep the fear from showing on his face. Cas knows his real name. Cas knows the Lightbringer. Cas probably has Dean’s rap sheet, from the teenage pickpocketing all the way up to the big cons.

But he can’t panic. Jo and Charlie are relying on him, not to mention Sam. 

Dean has been in worse hot water than this. He can have a cool head when it counts. He just has to take a step back, mentally assess the situation and make a plan. He’s Dean fucking Winchester - he can get anyone to fall in love with him. He can get Cas to tell him what Dean needs to know to get the hell out of dodge.

Stall. He has to stall. Jo and Charlie will hopefully carry on without him. If he doesn’t drag the FBI to their doorstep, they have a chance to get out of this scot free. 

He asks after a beat, “And they thought you’d do a better job getting me to spill?”

“We do have a more profound bond,” Cas says seriously.

Dean laughs, the sound dark and ugly. “I don’t even know you. Is your name even Cas?”

“Castiel.”

Dean’s retort falters on his tongue. “What?”

Cas says, a tad impatient, “Agent Castiel Novak.”

Dean blinks. “Do you always introduce yourself with Agent in front of your name?”

“Most of my interpersonal interactions are with other members of the Bureau, so yes.”

Dean grits his teeth at Cas’s words, phrased in the exact same stupid, awkward, way he has always spoken with Dean. Dean _had_ found the whole bewildered accountant thing endearing; now it makes Dean’s blood boil. If Cas thinks that’s the way to get Dean to open up, by preying on Dean’s old feelings, he’s sorely mis-fucking-taken. 

Just because Cas won’t drop the act doesn’t mean Dean will be the same easygoing, gullible mark he was before. He’s playing Dean’s game now, and Dean’s the reigning champ, recent fuckups aside.

Focus, he has to _focus._

Dean shakes his head in a weak attempt to clear it from a haze of shock and anger. “Do you want something to drink?” he asks, his voice stilted.

Cas starts. “Excuse me?”

“If you want me to sing like a canary, we’ll be here a while,” Dean says as he takes a couple steps backwards towards the kitchen.

“I don’t need anything,” Cas says as he crowds back into Dean’s personal space. “And I’d appreciate it if you don’t sneak off to alert your co-conspirators or slip something into my drink.”

Dean scowls. At least Cas doesn't seem to have all the intel on Charlie or Jo like he does Dean. “I work alone,” he tries.

Cas is quiet for a moment, brows furrowing as he thinks about something. “What’s the payload?” he asks, eventually.

Dean blanches as the full implications of Cas’s word choice sink in. “How do you know about that?” he demands. “Do you have this place _bugged?_ Have you been listening in on my conversations?”

Cas's expression hardens. “We’ve been monitoring your apartment for some time now.”

Dean resists the urge to go tear his apartment apart and instead stays exactly where he is. “How long?"

“One month.”

Right around when the dates with Cas started. Awesome. 

“What can you tell me about the Lightbringer?”

Dean taps his finger against his chin. “I dunno. That’s a pretty vague question.”

Cas’s eyes flash. “Do you know his associates? Do you know where he resides?” he presses, “Do you even know his real name?” 

Dean shrugs. “Maybe.”

Cas actually fucking growls as he surges forward to pin Dean against the wall. With one arm braced against Dean’s sternum, he hisses, “You are being _insufferable.”_

Dean’s mouth spreads into a lopsided grin, mocking and designed to cut. “Not for nothing Cas, but the last time you had me like this, I thought I was gonna get laid,” he retorts.

Cas backs off like Dean’s burned him. Dean stumbles as he regains his footing. 

“This is useless,” Cas announces in a carrying voice. “I’m bringing him in. Agent Milton, stand by.”

Dean grins as Cas pulls out the handcuffs. “Getting kinky, already?"

If looks could kill, Dean would be a soot stain on the floor.

* * *

“Don't I get a phone call?” Dean hollers. He must’ve been stuck in this interrogation room for hours, mostly alone. After Cas brought him in, he was hustled past a boatload of Feds. Most didn’t bother to hide their blatant gawking. Apparently Cas's staring habit is a Bureau-wide problem. Weren’t these people supposed to be secret agents?

They first tried to get some junior agent to work him over, but Dean stayed stubbornly uncooperative. At the start, he probably should have tried to butter the agent up, but Dean was still so pissed off about Cas he blurted the first thing that came to mind: “Did you take a wrong turn on your way to your boy scout troop?”

Agent Alfred “I Can’t Grow a Beard” Samandriel did not stay long. 

Without his phone, Dean has no way of knowing if Jo and Charlie got out. Or the time. His biological clock says it’s probably around eleven at night; he’s not about to pass out from exhaustion yet, but give him time.

The door opens, and Cas steps inside next, carrying an armload of files.

“Hey, it’s Agent the Original Flavor,” Dean says as he adopts a bright grin. “Here to bust me out?”

“No.”

Dean sighs wistfully. “A man can dream.”

“Dream smaller,” Cas says flatly as he dumps his papers on the table. “I need you to look these over and let us know if you recognize any of these photos or aliases.”

Dean crosses his arms across his chest. “Not without my phone call.”

Cas rubs at his temples. “You don’t get a phone call, Dean.”

Dean’s face darkens. “I don’t get a what now?” he asks, his voice deadly quiet.

“Phone calls are a privilege,” Cas says shortly, “not a right, at the FBI. You are entitled to a lawyer, however.”

“This is why I hate procedural cop shows,” Dean mutters under his breath. He raises his head to meet Cas’s penetrating gaze. “Alright the phone call BS aside, why should I tell you anything? What’s in it for me?”

“I am prepared to make a deal.” He pulls a slim file from the bottom of the stack. He skims it briefly, saying, “In return for information _and evidence_ pertinent to our investigation into Nick Lightman and his criminal network, we can reduce the charges against you.”

“Nick?” Dean repeats.

“You don’t even know the Lightbringer’s real name?” Cas asks, distinctly unimpressed.

Shit.

Dean shakes his head, and Cas’s face falls. “Why would I?” Dean asks. “I’m the low man on the totem pole doing all the dirty work. If you wanted someone with answers, you should’ve gone for the handlers. They have a direct line to the big man upstairs. So I’m gonna need that phone call now,” Dean says evenly. 

“No.”

“I need to call her if you want evidence,” Dean says, a hint of steel in his tone, “and since you can’t lock up someone like the Lightbringer on hearsay, she has it. I don’t.”

But Cas doesn’t make a move to leave. Instead he sits there, staring at Dean like he’s trying to read his mind through intense eye contact alone. 

“What?” Dean snaps, fed up with the tense silence between them. “Aren’t you gonna see about that phone call?”

Cas taps the folder in front of Dean. “If you verify a few names for us, I’ll give you that call.”

Dean’s anger flares. “How do I know you’re telling the truth? You could just be playing me for a freebie.”

“You’ll just have to have faith.” Cas says frostily. “Since you’ve given us nothing so far, I’m not at liberty to discuss anything with you.”

“I’m not really the praying type, Cas,” Dean shoots back. “And you’ve been lying to me since day one. My trust’s in short supply these days.”

“Fine.” Cas stands up. “I’ll tell my superiors you were uncooperative, and you’ll be formally charged with your crimes in the morning. Good night, Dean.”

Dean glares up at him, sheer hate in his eyes. “Wait.”

Cas pauses, his face blank. “Yes?”

Goddammit, Dean can’t get a read on him _at all._ All the patterns and signs he’d come to recognize in Cas - in Cas’s _act,_ the one he fell for - are useless. For fuck’s sake, he doesn’t even know if Cas is into men. He might even be married. He might have _kids._

Dean could try to charm him again, but Cas has already had a peek at the man behind the curtain - any effort would probably be a total waste. Agent Castiel has so far exhibited nothing but disdain, frustration, and annoyance with him. Dean can fake a miracle for a con, but he’s never had much luck with the real deal. And it’d take a goddamn miracle for Cas to give him an inch.

Dean pulls the files towards him. “Three names,” he says through gritted teeth. “I’ll give you three names to prove my goodwill towards Big Brother.”

“Ten.”

“You’re fucking nuts. Four.”

“Seven.”

“Five.”

Cas sits back in his seat to listen, the smug son of a bitch. “Five it is.” 

* * *

“I pulled a Lost Heir with her,” Dean says, tapping a grainy surveillance photo, “Krissy Chambers.” He swallows. “She mentioned she has a dad, Lee, also working for the Lightbringer - or kidnapped by the Lightbringer. She wasn’t real upfront about it.”

* * *

“We worked a Turnabout together. I don’t think she gave me her real name - hazards of the trade, you get it -” Cas squint says he very much _does not get it_ \- “but she told me she was Kaia Nieves.”

* * *

“Walt and Roy. No last names that I know of, since our Snipe Hunt was a day - two max. They specialized in those - not the long cons. They seemed real chummy though, so wherever they are, I bet they’re probably still working together. ”

* * * 

“I did a Pigeon Drop with Jody Mills last year in between my own cons. I think the Lightbringer has something on her wife. He didn’t have her locked up, but he had bad enough dirt to rope in Jody. She’d flip in a heartbeat if Donna would be OK.”

* * *

“Gordon Walker? I recognize the name,” Dean says with a grimace as he shoves a phone transcript back towards Cas’s end of the table. “He’s a pro at the Spanish Prisoner. Never had the bad luck to work with him, though. I heard he’s a nasty son of a bitch.”

* * *

“And this man? Do you know him?” Cas asks, pointing to a mugshot of a dark-haired man. “We think his real name is Mick Davies.”

Dean doesn't speak. Mick was Sam’s handler before Sam took over the gig, managing the cons for Toni and Ketch. Mick got caught by the Feds last year, and Sam never saw him again. Rumor has it, he got extradited back to the UK.

“Since apparently they didn’t teach you to count at Quantico, this is the sixth name you’re asking for,” Dean snipes as he pushes the files away. “I’m not saying another damn thing.”

“Alright,” Cas says. To Dean’s surprise, Cas doesn’t get up from his seat. Instead, he reaches inside his suit pocket and pulls out a cell phone. “Here,” he says.

“I don’t have to do this on a fancy FBI phone?” Dean asks, eyebrows raised. He doesn’t take it.

“It is my phone and I am FBI,” Cas says, unsure. “I don’t know what would make it fancy, though.”

Dean plucks the phone from Cas’s fingers. It’s not locked, and Dean still can’t make heads or tails of the man sitting across from him. “Dude, you have Angry Birds on here?” he says before he can stop himself. He can’t for the life of him picture Cas killing time and playing Angry Birds - fake accountant Cas or Agent Cas, for that matter.

Cas shrugs. “Yes. I still cannot figure out why the birds are so angry in the first place.”

Dean scowls at the return of Cas’s awkward, clueless act. What a dick, rubbing it in Dean’s face.

He scrolls through Cas’s contacts, a little surprised at how short it is. Most have the last name “Novak.” 

There is also a contact for a John Paul Jones, and Dean has to snort. What are the fucking odds Cas has Led Zeppelin’s bassist on speed-dial? Then again, Dean knows fuck all about Castiel Novak. It could be the real deal. More outrageous things have already happened to Dean today.

Dean dials Charlie's number by heart. 

“It’s me," he says before she can get a word in. “Are you on the move?”

 _“ Dean?_ Where the hell are you?”

“Please tell me you’re not still in LA.”

“No, but still in California.”

Dean sighs. “Good enough. Look, I’m at the FBI.”

Charlie actually yelps. “What the fuck?”

“I’m hoping you'll help me out.”

Charlie is quiet for a moment on the other end of the line. “Dammit.”

“Look,” Dean says before she can tell him to fuck off, “I'm not asking you to turn yourself in. It’s just... you got info that could help me. And I know you can send it over without getting caught by the Lightbringer _or_ the Feds.”

“Flattery will get you everywhere,” Charlie mutters begrudgingly. 

“So you’ll do it?”

“Are you going to make a deal?” Charlie asks instead of answering his question. 

“Probably.”

Charlie is silent.

“...Should I not?” Dean asks as Charlie's opinion remains a conspicuous no-show. 

“I’m thinking.”

“Think faster,” Dean says in a low voice. “My life is kind of on the line here.”

Cas fidgets in his seat while Dean waits. He can hear Charlie typing away on the other end as Cas says, “We won’t kill you.”

“No,” Dean rolls his eyes, “you'll just shove me in a super max and leave me to rot.”

“Nonviolent offenses hardly ever-”

“I was exaggerating, dude-”

“Your tone did not make that clear-”

“My _tone-”_

“Am I interrupting something?” Charlie cuts in over Dean’s responding retort. 

“No,” Dean says, not at all petulant. “What’s the verdict?”

“Let me in on the deal.”

_“What?”_

“We’re on the run,” Charlie says, typing noises increasing. “It’ll be a hell of a lot easier if we’re not hiding from the government _and_ the Lightbringer.”

“Okay,” Dean says, his gaze flicking up to Cas, sitting placidly in his chair, apparently content to do nothing but listen in on Dean’s side of the conversation. “I can try to swing that for you.”

“Good. And Jo too.”

Dean runs a weary hand down his face. “Yeah, sure. Why not. The more the merrier.”

Charlie snorts. “How’d they catch you, anyway?”

Dean fiddles with the papers on the table, unable to look at the agent across the table. “It was Cas.”

“Cas turned you in?” Charlie says, shocked.

“Agent Cas Novak brought me in,” Dean says in an undertone.

 _“Oh,”_ Charlie says, and Dean can hear her fucking snickering on the other end of the line.

“Charlie!” he protests, eyes going wide as he whips up his head to stare at Cas, now looking intrigued. “Shit, should I not have said your name?” he asks Charlie. “He’s right here with me.”

Charlie snorts. “Come on, like _Charlie Bradbury_ is my real name.”

“It’s not?”

“You’re cute when you’re dumb.”

Dean groans. “Stop laughing.”

“You gotta admit, it’s a little funny.”

“It’s really not,” Dean says darkly. “I’m in deep shit here.”

Charlie sucks in a breath. “Sorry. I’m still kind of reeling. It’s a lot to process.”

“Yeah, I get that. It’s a lot for me too.”

“Tell Cas I’ll text him a link to contact me. I don’t trust the Fed channels. Send over the deal, and I’ll send over the intel.”

“You swear?”

Charlie laughs. “I’ve never gone straight before. Could be fun.”

She hangs up.

* * *

As soon as Cas takes his phone back, it pings with a text.

“That’ll be Charlie’s secure channel,” Dean says as Cas reads the message. “She said to send over the deal, and she’ll hand over the dirt.”

Cas tucks the phone back in his suit jacket. “Good.”

Dean runs a hand down his face. The exhaustion that had been building since his late night phone call has sunk into his very bones. He’s had to be _on_ all day, from the moment Crowley woke up in the morning until now.

“She wants to go in with me,” Dean tells Cas. “Turn over what she has to you guys in return for whatever you’re giving me.”

Cas’s mouth drops open. “That’s good news,” he says faintly.

“She’s the best tech in the business,” Dean says. “If you want intel, Charlie’s your gal.”

“But she was your handler,” Cas argues, his brow furrowing.

“So?”

“I would have expected handlers to be more loyal to the organization. They are closer to the top and more trusted than the average employee.”

Dean grimaces at the word _employee_ \- like working for the Lightbringer came with PTO, a 401K, and dental. “Not Charlie. She’s always done her own thing, even before she joined - she wasn’t conscripted like the rest of us.”

Cas tilts his head. “Conscripted?”

“Blackmailed,” Dean says flatly. “That shit I told you, about Krissy’s dad and Jody’s wife, they’re the rule. Not the exception.”

Cas's eyes gleam. “People aren’t loyal to blackmailers. If we can take away the leverage, we could flip a lot more people than just you and your handler.”

Dean nods. “And my partner.”

“Partner?”

“She wants to be included in the deal too,” Dean explains.

“You have a partner?”

Dean smiles wryly. “You said I wasn’t talented enough to pull off cons all by my lonesome.”

Cas doesn't look the least bit vindicated by the news he was right. He gives his head a slight shake. “What does Mr. Lightman have on you? I assume you are also part of the rule and not an exception.”

Dean’s jaw clenches as he looks away. He doesn’t say anything.

“Does he have your brother? Sam?”

Dean nods once, the barest tip of his head.

“The one you raised,” Cas goes on, and Dean would rather face the Lightbringer himself than talk to Cas about Sam. He told Cas about Sam _in confidence,_ and now Sammy’s name is gonna be splashed over FBI transcripts and recordings. Fucking great.

Dean shakes his head. “He was an easy kid,” he says begrudgingly, “practically raised himself.”

“No child can raise himself,” Cas argues, his eyes laser-focused on Dean’s face.

Dean shrugs. "Sammy did. Don't know what else you want from me."

Cas sighs. “If you insist,” he says, and Dean can tell he just said that to placate him. Fine - it’s not like Dean cares if Cas thinks Sam is the best thing since FM radio.

“About that deal-” Dean starts, but Cas cuts him off.

“It’s late.”

“So?” 

“I’m tired, and I think you are too,” Cas says pointedly.

Dean’s mouth thins into a line. “You don’t know a damn thing about me,” he lies through his teeth.

Cas shoots him a pitying look, like can see right through Dean’s bullshit, and gathers his files together in a neat stack. “We can resume discussions in the morning.”

Dean throws up his hands. “You’ve got to be fucking kidding me,” he says loudly. “We can’t do this now?”

“No. My superiors need to-”

“Fuck your superiors,” Dean snarls.

“-be here during the negotiations and they have all gone home for the day,” Cas continues like Dean’s interruption didn’t happen.

“Fuck you too.” Dean stares around the room. “Am I supposed to sleep on the table?”

“What? No,” Cas says, outrageously offended on behalf of the US government. “We have quarters downstairs.”

Dean sighs as he gets to his feet. “Brilliant,” he mumbles as Cas walks to the door. “It’s not like it’ll be my first night in jail.”

* * *

They come for Dean at what feels like the ass crack of dawn. The room Cas stashed him in has no view to the outside world, so Dean has no idea what time it is until they take him up to ground level and escort him past a window flooded with weak early-morning sunlight.

Cas is already waiting in the interrogation room.

“Hello, Dean.” He hands Dean a breakfast sandwich and a cup of coffee. 

Dean grimaces at the foul sludge. He mumbles, “What time is it?”

“Six thirty-four am,” Cas says promptly. Dude didn’t even look at his watch.

Dean chokes on his next sip. “Thanks, HAL.”

Cas tilts his head, eyes narrowing. Dean burns with embarrassment at the familiar sight. “Come on,” he says harshly, his tone laced with disbelief, “have you seriously never seen 2001: A Space Odyssey?”

Cas shakes his head. “I don’t have a lot of time for films - or is that a novel?”

The door opens before Dean can answer, and two agents walk in.

“Agent Milton, Agent Balthazar,” Cas greets.

Dean glares at the redhead he’d met twice before, and the new guy. “‘Sup,” he growls, toasting them with his sandwich.

Balathazar grins. “I wouldn’t try any science fiction with Cassie. Poor lad grew up under a rock or something.”

Cas’s neutral expression sours. 

“Or comedy... or drama, or mystery for that matter,” Balthazar continues as he swings the chair around to straddle it and hug the back.

 _“Thank you,_ Agent Balthazar,” Cas says through gritted teeth.

Balthazar winks at Cas, and Dean’s jaw clenches. “Just making conversation. It’s too early for an interrogation.”

“Yes, it is,” Milton sighs as she takes her seat. “But let’s get started anyway. Uriel wants this matter taken care of as soon as possible. Cas brought us up to speed with what you discussed last night after he brought you in.”

“When?” Dean asks, baffled.

“This morning.”

Cas’s lips purse as Dean’s gaze swings back to him. “I don’t sleep much,” he mumbles.

So Cas said before.

Dean’s face hardens as he deliberately faces Milton. “I want a deal.”

“Yes, we know that,” Balthazar says as he rolls his eyes. “Quite a one-track mind.”

“It’s my ticket outta here,” Dean says, eyes narrowed. “It’s a little important to me.”

“We understand,” Milton intercedes. She flips over a stapled document in her stack and pushes it towards Dean. “Here is what we are prepared to offer.”

Dean scans the first page, careful not to transfer any grease stains from his sandwich. It’s not totally filled with legalese and jargon, but enough to make Dean uncomfortable.

He switches to the second page. More of the same.

“We have sent a copy to your associate,” Milton says as Dean looks up. “She has yet to respond.”

Dean skims the top page again. “I don’t see anything about my brother.”

“Your brother?” Balthazar repeats. 

“I want the same deal for him. I need to make sure he’s safe too - especially if the Lightbringer’s goons come knocking.”

Cas turns to Milton and Balthazar, a clear _I told you so_ on his face.

“Well-” Milton starts, but Cas cuts her off. “Can I have a minute with Dean alone, please?”

“Cassie,” Balthazar warns.

Milton says severely, “This isn’t the plan we agreed upon.” 

“Do you want him to sign the agreement?” Cas says, eyebrows raised. “This is the way to do it. Dean won’t do anything without ensuring Sam’s safety.”

Dean’s face darkens. Sam’s name shouldn’t be said anywhere near this place.

“Fine,” Milton says. She stands. “But you’ll owe me, Castiel.”

Balthazar whistles, his sharp eyes darting between Milton and Cas.

Cas waves his hand. “Fine. Leave, please.”

“Five minutes,” Milton warns before she ducks out, Balthazar lagging behind her.

“What’s going on?” Dean demands. He warily glances around, noting the camera in the corner of the room. Is it still on?

Cas’s gaze skitters around the table before landing on the stapled papers in Dean’s hand. He reaches over to tap the pages once before retreating. “We have an inside man. This is the exact same deal we offered him.” 

“Okay,” Dean says slowly, and the lack of eye contact (Cas’s favorite pastime) is telling, “and the problem is you can’t give me a different one?”

“You were included in his deal.”

Dean’s pulse spikes. “Did he rat me out?” he demands, both hands thumping on the table. “Whatever that bastard promised you-”

Cas’s eyes widen, shocked. He says quickly, “He told us where to find you so we could gauge your loyalty to Mr. Lightman’s organization before bringing you in.” Cas scowls. “He insisted it was unnecessary, but we needed to make sure.”

Dean sits back in his seat. “Uh-huh,” he huffs, not entirely on board. 

Cas pulls his phone out of his pocket. “You can talk to him. He can explain.”

“Fine.” Dean glances at the contact Cas dialed (John Paul Jones) before holding it up to his ear.

It rings once.

“Castiel?” a man on the other end whispers. “It’s pretty early, dude.”

Dean can’t breathe for a moment. He recognizes the voice, and it's _not John Paul fucking Jones._

“You there?” Sam asks into the silence. “This isn’t another butt dial, is it?”

Dean swallows and says, “Did I interrupt your beauty sleep, Princess?”

_“Dean?”_

“Hey, Sammy.”

“You’re calling from Castiel’s phone.”

“Beats me why I keep calling you the genius in the family,” Dean says weakly. “You can barely manage caller ID.”

Sam huffs a strained laugh. “So he finally brought you in?”

“Pretty much,” Dean says as he side-eyes Cas, “You’re their inside man?"

“Yeah,” Sam breathes.

Dean lets his head fall into his hands.

“How do you think I pulled together that safehouse in South Dakota?” Sam continues, his tone wry. “It’s all part of my deal. Is Novak following through?”

“Yeah… we were just getting to it.” He sighs, scrubbing the heel of his palm down his face. “You’re really part of this?” 

“I needed to get you out,” Sam says, and he sounds so guilty. “It’s been killing you, dude.”

“Sam…”

“I know we don’t talk about it, but you can’t expect me to sit by while you have to… sell yourself to the marks.”

Heat flares up Dean’s neck like a wildfire, and thank god Cas can’t hear Sam’s half of the conversation. The whole thing is probably being recorded, but at least Dean doesn't have to look at Cas’s face while his brother calls him out for basically being a whore. 

“You _hate_ the marriage cons,” Sam continues, “so I saw an opening and I took it.”

His little brother is such an idiot; Dean could strangle him. “What if _he_ catches you? Do you know what Lilith does to snitches?”

“It was worth it,” Sam says stubbornly. 

Dean glares at Cas across the table. Somehow, some way, this is all his fault. He probably appealed to Sam’s hero complex, his touchy-feely soft side, and Sam played right into his hands.

Cas’s brow furrows.

Dean tries to focus back on Sam. “So, this deal you made. What _exactly_ did it entail?”

“Immunity for all fraud and embezzlement charges; reduced charges for theft and money laundering,” Sam lists, “Anonymity during the trial testimony; WitSec if we can prove we are in danger of bodily harm.” Sam adds, “Which we can.”

Dean sets the deal down on the table. That was basically what he got out of it too, but Sammy was always more legalese-savvy, even if he never made it to law school.

“Right.”

“And a clause about how you were gonna get the same deal if you were an asset to the investigation.”

Dean drops his head into his hands. “Well, you can mark that one down as followed through.”

“Good,” Sam says, and Dean can hear the sheer relief in his voice. “And did Novak-”

The door opens, and Milton and Balthazar reenter. Dean’s head snaps up, and he loses whatever Sam asks him next.

“Hold on,” he says. “More Feds just walked in.”

“Hang up,” Balthazar orders. “You verified that every precious hair on your brother’s head is going to be looked after.”

Dean frowns up at him, telling Sam, “I can’t believe you’ve been dealing with these dicks for - hey!”

Balthazar hands Cas’s phone back to its owner with a smirk. 

“Hello, Sam,” Cas says, and Dean’s fists clench at the touch of familiarity between them. “We have to continue our discussions here. Dean will be in contact later.” He pockets his phone.

Dean glares at all three of them.

“Now,” Milton says as she sits back down. “Where were we?”

* * *

Dean signs the deal. He spends the whole morning and afternoon in that damn room, confirming accounts and providing information on every single person he ever worked with in the Lightbringer’s organization, starting from that botched job in Lincoln ten years ago up until his most recent marriage con.

Charlie sends her information dump around noon.

After they break for lunch, Cas, Milton, and Balthazar come back with their superior, Uriel - the head honcho in charge of everything. He rubs Dean the wrong way, as supercilious as Balthazar without the charm, and as detached as Milton without the kindness.

“And Mr. Lightman has a definite connection to Mr. MacLeod?” Uriel asks.

Dean nods. “We’d come into the job expecting Jo to pull off the main con, since I had just worked the Trent job. But our orders came in, and Crowley was the next target.”

Uriel’s eyes narrow. “Why?”

“I’m not sure,” Dean admits, “but I think Crowley personally fucked him over in the past. He had an emergency stash of cash under the floorboards in his bathroom. A rich guy’s bug out bag.”

“Yes, we did know that,” Milton says, to Dean’s surprise.

“You did?”

Milton shares a look with Cas. “He called it in missing to the authorities last night,” she says after a beat.

“It was probably his escape plan,” Dean says. “If I fucked over the Lightbringer, I’d watch my back and have an out. He’s not really a forgiving type.”

Balthazar leans in. “He _did_ send you in to exact his revenge.”

Dean shrugs. “That’s what I think happened, anyway. If I still had access to Crowley’s financials, I could maybe put two and two together. Get you a dollar amount, a date, or something - especially in combination with whatever Charlie dug up. Tie the two of them together with a paper trail. The guy’s good, but I’ve been learning his tricks for the past two months.”

“I don’t think we can get you access,” Cas says, his eyes regretful. “Mr. MacLeod’s firm is very resistant to government intervention and investigation.”

Dean snorts. “Of course they are. They’re up to all sorts of shady shit.”

Milton’s nose wrinkles. “Unfortunately, most of it is legal.”

“Crowley does love his loopholes and grey areas,” Dean agrees.

Uriel surveys Dean with a long, cool look. “That he does,” he says slowly, his expression calculating. “But you had access before.”

“When I was his personal assistant,” Dean says slowly, “but I didn’t show up for work today, so Crowley’s going to be pissed. He’s fired people for a lot less.”

“Not ones he was sleeping with,” Uriel says.

Alarmed, Cas opens his mouth. “Uriel, you can’t possibly-” 

Uriel continues as if there was no interruption, “Say you go back into work with a decent explanation tomorrow. You could get this information for us.”

Dean frowns, glancing between Cas, who looks more distressed with every word out of Uriel’s mouth, and Uriel, who looks incredibly pleased with himself. “Yeah, maybe.”

Milton nods, apparently caught up with Uriel’s eagerness. Her eyes widen as she turns to him. “If he goes back-”

“Better yet,” Balthazar adds, “he could finish it.”

Uriel sits back in his seat. “ We’ve been trying to lure Lightman out of hiding for years. However, if he always attends the weddings...”

Cas, his face horrified, slams his hands down on the table. “No,” he says as they both turn to him in surprise. “Dean did _not_ sign up to continue with the con. He _just_ took our deal. You can’t ask-”

Dean had spent the past how many hours rehashing all his past misdeeds, all the people he scammed, all the decent people he duped and practically left at the altar. The guilt sits unbearably heavy on his shoulders. 

And this whole bullshit with Cas taught him a lesson he never thought he’d learn: how fucking shitty, infuriating, and _embarrassing_ it is to be fooled by someone you thought you knew.

“I’ll do it.”

Dean blinks, the words slipping out almost unbidden. Almost.

If they do manage to pull it off, if the Lightman gets put away, Dean will finally be free. But the thought doesn’t cheer him at all.

“What have I got to lose?” he chuckles, the sound beyond bleak. “I already have the research and the in. You guys’ll take care of Sam. And I’ll be helping people,” he adds, and while the agents don’t care about his logic, he has to say it aloud anyway, just for himself. “I’ve always wanted to do something like that.”

“You never said,” Cas murmurs as Balthazar crows his delight with a triumphant, “Yes!” and Milton nods, a wide smile splitting her face. 

Dean numbly pulls his shaking hands into his lap and waits for instruction.

* * *

They let him go at five-thirty on the dot.

“But no returning to your apartment,” Milton says as she stows away her tablet in her briefcase.

Balthazar stretches, hands raised over his head. His spine pops.

Dean purses his lips. “I’m gonna need clothes to wear tomorrow.”

“We had an agent pick up necessities earlier today,” Milton says. “We can’t allow you anywhere without a detail, so you’ll be staying here for the time being.”

Dean rolls his eyes. “How can I wine and dine Crowley with a babysitter?”

Uriel stands. “You will obviously be allowed to go to work and on necessary excursions.”

Dean grimaces. “Awesome.”

Balthazar opens the door, and Milton and Uriel file out without looking back. “Cassie, are you coming?”

Cas stands. “I’ll escort Dean downstairs.”

“Fantastic,” Balthazar drawls. “Just make sure Samandriel isn’t on duty. I don’t think he’s quite recovered from meeting Mr. Winchester the first time.”

Dean smirks as he gets to his feet and prepares to leave, but Cas pauses in the doorway. After a fleeting glance around them, he lets Milton, Balthazar, and Uriel drift out of earshot.

“Whatcha doin’, Cas?” Dean asks, wary. He surreptitiously peeks at the security camera in the far corner of the room.

Cas turns to face Dean. “Would you like to come with me to my apartment tonight?”

Dean rears back, his mental warning bells going haywire. “Why?” he demands.

“Because you need a place to sleep,” Cas grumbles, rolling his eyes like he can’t believe he is having this conversation. 

Neither can Dean.

Dean crosses his arms across his chest. “And what’s it going to cost me?” he demands. “I know this time it ain’t a round of Parcheesi.”

“Nothing,” Cas says, still a little too shifty-eyed for Dean’s taste. 

Dean scowls. “A blow job?” he asks bluntly. “A full on fucking? Just because of my… history _does not mean I-”_

“No, no, nothing like that,” Cas interrupts, hands flailing as he tries to shut Dean up.

“So what is it?” Dean hisses through clenched teeth. “I’m not going anywhere with you until I know what you want from me.”

 _“Nothing,”_ Cas stresses.

“I wasn’t born yesterday,” Dean says stubbornly. “There’s no such thing as a free lunch.”

Cas shakes his head. “This is not a ‘free lunch,’” he says. 

Dean’s eyes narrow at the ridiculous air quotes. Haven’t they moved past Cas’s stupid act? Dean’s shown, all fucking day, he’s gonna play ball with the agents. Cas doesn’t need to keep jerking him down that deader than dead end.

“Just drop it,” he mutters darkly.

“Why?” Cas asks, genuinely confused. “You need an agent escort, and I am offering. My apartment is much nicer than the quarters downstairs. It would be just to sleep, I swear.”

Dean glares. “I don’t trust a word outta your mouth.”

The corners of Cas’s mouth tighten. “Understandable, I suppose.”

“Yeah, so,” Dean gestures for them to get a move on.

Cas sighs. “If you insist.”

They get halfway down the hallway before Cas says, “My spare bedroom has a very nice mattress. Memory foam.”

Dean fights down his baser instinct to jump at the offer. Mouth shut, he marches a little faster than Cas to the elevator.

“You said you were very fond of that type,” Cas continues from behind him. And yeah, Dean once waxed poetic about the one time his digs were outfitted with a nice bed, but that was over his morning coffee with Cas - a time and place Dean is _not thinking about right now._

Dean jabs the down button impatiently.

“The door also locks.”

Dean whirls on him. “Why are you so dead set on getting me back to your place, huh?” he demands. “Say I believe you, that you don’t want any hanky-panky goin’ on, _which I don’t._ What’s your deal?”

Cas’s mouth does a few funny movements as he tries to think of what to say.

Dean barely keeps himself from ordering Cas to spit it out. He barks instead, “Don’t overthink it, dude.”

“You deserve better than the cells downstairs,” Cas blurts, going a bit red in the face.

Taken aback, Dean doesn’t have an immediate retort.

“You are a good man, and you are cooperating fully - more even, than we expected,” Cas says, staring hard at Dean. “You should be given a place to stay that does not regularly house criminals and enemies of the state.”

“But that’s what I am,” Dean says stupidly.

“No, you’re not,” Cas says, shaking his head. The elevator dings its arrival, but neither of them take a step forward. As the doors start to close, Cas repeats quietly, “You deserve better.”

Dean sighs and instead jabs the up button. “I hope you have good water pressure.”

He is so going to regret this.

* * *

Cas opens the door of a fourth floor fancy condo five minutes’ drive from the FBI headquarters.

Dean stops dead in his tracks.

This is more what he expected from the Cas he thought he knew. Papers and files strewn over every surface. A fine layer of dust on the screen of the television in the living room beyond the short entryway. Dean takes a couple steps further inside, and Cas’s kitchen is minuscule compared to the one in the beach-side bungalow. There’s a stove, a sink, and a refrigerator barely more than a mini-fridge. 

“Sorry I didn’t clean,” Cas mutters as he edges around Dean and his suitcases to toe off his shoes.

Dean backtracks and hurriedly takes his off too.

Cas hangs his coat on the hook by the door and shrugs out of his suit jacket. “Your room will be there,” he says. “This is mine.”

“Is the other place even yours?” Dean asks as he walks around Cas to inspect his new room. He dumps his stuff at the foot of the bed.

“No, it belongs to my brother,” Cas calls.

Dean pokes his head out. “The one who gave you the Lincoln?” he asks before logic catches up with him. He could bang his head against the wall.

There’s no guarantee anything Cas ever told him was real. Dean normally would even doubt he has a brother, but Cas already confirmed it. And Dean would _definitely_ doubt Cas owns the Lincoln, but unfortunately the drive over from the FBI proved otherwise. He braces for a derisive snort or an equally devastating gentle correction.

He doesn’t expect Cas to respond, “Yes, that’s him. He is a chef at _Trickster,_ if you’ve heard of it.”

That explains the over-the-top kitchen.

“I haven’t,” Dean calls as he exits his bedroom.

“If you have a sweet tooth, I recommend it,” Cas says as he opens his fridge and frowns at the empty shelves. “I’m afraid I don’t have much in terms of dinner.”

“It’s fine.”

“I usually eat at the office and get home much later than this,” Cas explains as he turns back around.

“It’s really not a problem,” Dean says. “I have energy ba-”

“Do you prefer pizza or Chinese?” Without looking up, Cas pulls out a couple of take-out menus from a drawer. “I can also get Thai, but that would take longer. I have a flyer from a,” Cas squints, “Polish restaurant, I think, but I haven’t ordered from them before.”

“Pizza is fine,” Dean says, taken aback by the choice. “Get whatever you want on it.”

“You said you liked meatlovers.”

Dean transfers a few papers from the couch cushions to the coffee table, careful to keep them in the same order as he sits down. “When did I say that?” 

His preferred pizza toppings definitely didn’t come up in that interrogation room.

“About three weeks ago,” Cas says as he approaches Dean, two glasses of water in hand.

Three weeks ago plus Cas equals morning coffee date. Dean grimaces. It vaguely stirs his memory, a stray comment in the middle of stupid small talk he made about what he did the night before. Dean does love cheat day.

“Were you recording me the whole time?” Dean asks, more tired than angry at this point. He is almost positive he said nothing incriminating, but the mental image of Cas sitting in his office, listening to Dean believing every lie out of Cas’s mouth - maybe while Balthazar and Milton eavesdrop too - makes him want to dig a hole six feet deep and bury himself in it.

“At your apartment, yes.”

Dean shakes his head. “No, over coffee.”

Cas squints. “Are you asking me if I was wearing a wire? We are only authorized to use them for sting operations. Reconnaissance is too low-level for equipment use.”

 _Reconnaissance,_ that’s one word for it.

Dean says flatly, “So you just remember how I like my pizza because I said it once almost a month ago.”

Cas takes a sip of his water and shuffles a couple papers around, making more space. “I do.”

“Must be a useful skill.” Definitely an invaluable trick in a con. Nothing makes a mark feel wanted than remembering stupid shit about them like their favorite food or childhood pet. Even now, Dean can’t help the small curl of warmth behind his sternum. He brutally squashes it down.

Dean snags the television remote half-hidden under a book. “Do you mind?” He waggles the remote in Cas’s direction.

“Go ahead,” Cas says. “I’ll call for pizza.”

Dean flips on the TV and tries to settle in. He can feel Cas’s presence in the apartment like an itch under his skin, so he focuses on the screen instead. He might as well be wearing those horse blinder things. After some intense channel surfing, he finds a Dr. Sexy rerun on.

Maybe he can do his little new-place ritual here. He _is_ in a new apartment. He has Dr. Sexy, he has a drink (non-alcoholic, but beggars can’t be choosers), he just needs - 

Dean all but vaults over the couch. He bolts for his bedroom, not even bothering to turn on the lights, and rips open his overnight bag and suitcase, unzipping every flap and hidden pouch. He rifles through the garbage bag of wrinkled suits the feds packed up for him. He shakes out his shirts and pants in a fruitless effort to dislodge photos still probably stuck beneath the pages of a coffee table book on the Grand Canyon.

“Dean?” Cas asks, his shadow filling up the doorway.

Dean raises his head. “What?”

“Is everything okay?” Cas falters, taking in whatever expression is making its way across Dean’s face. He tacks on, uselessly, “...given the circumstances.” 

Dean shakes his head. “It’s fine.”

“Were you looking for something?”

“Just photos,” Dean says without looking up. “It’s nothing.”

“It doesn’t seem so,” Cas says slowly, cautiously, like he’s worried Dean will call him out for it. “What were they photos of?”

“My folks, Sam,” Dean says, “It’s fine - I’m sure they’ll turn up eventually.”

“Were they at your old apartment?” Cas asks.

“Yeah.”

Cas licks his lips. “They’re probably still there. I can get them for you.”

Dean straightens. “You could?”

Cas nods. “I can stop there after I drop you off at work. Your apartment is very close.”

“Right, of course,” Dean says, shoulders drooping. He asks dully, “What do you want for ‘em?”

“What do _I_ want?” Cas asks, eyes narrowed. He takes a step back, studying Dean’s face closely. 

“Yeah.” Dean splays his hands wide to gesture up his whole body. 

Face thunderous, Cas grabs Dean’s upper arm and all but hauls him into the brightness of the living room. “Will you stop assuming you count as some sort of bargaining chip? I _will not_ take advantage of you.”

Dean opens his mouth to retort, but Cas is not done. “I asked you here under no false pretenses. I am _offering_ to do something for you because it will make you happy, and it is a relatively easy matter to see to. That is it _._ Not everything has hidden meaning and subtext. Sometimes a favor is just that, a _favor.”_

Dean stalks back to the couch, calling over his shoulder, “Not in my experience.”

“You are insufferable,” Cas says haughtily. “Has anyone ever told you that?”

Dean shrugs. “Most people think I’m adorable.”

Cas grumbles incoherent words that don’t sound at all like an agreement. "I'm going to clean," he says, spinning on his heel and disappearing out of Dean's field of vision. 

Dean shrugs and turns back to the television. "You do that."

Twenty minutes and three dead patients later, the front door closes, and Cas appears, pizza box in hand. “What is this?” he asks as he sets the box down on the coffee table.

“Dr. Sexy, MD.”

“That’s not how to administer CPR correctly,” Cas says, squinting at the screen as if that will improve Dr. Piccolo’s technique.

“It’s a soap opera, Cas,” Dean says, rolling his eyes. He grabs the box and opens, mouth watering at the smell of gooey cheese and sausage. “It’s not supposed to be accurate.”

“But her hand position was all wrong,” Cas complains as he leaves for the kitchen. “And her compressions were not nearly forceful enough to have an effect.” He returns, two plain plates in hand. 

“Nobody watches this for a medical how-to book,” Dean says, gesturing to the screen. “Watch, the intern is gonna fuck Dr. Wang in the supply closet before the next commercial break.” He takes a bite, closing his eyes in bliss. Damn, it feels like he hasn't eaten all day. 

“That can’t be sanitary,” Cas says, completely focused on the television. His pizza cools in his lap. 

“It is sexy, though.”

“Is this what most soap operas are like?” Cas asks curiously.

Dean polishes off his first slice and turns to him. “Haven’t you seen one before?”

“Maybe once or twice, not enough to gain a full grasp of the genre.”

“Dude, that's all you need for _a firm grasp of the genre.”_ Dean narrows his eyes, suspicious, before grabbing another piece of pizza. “Some chick gets murdered here; a guy finds his long lost twin there. A new love triangle and secret affair every season.”

“So any combination of improbable situations,” Cas surmises, more or less correctly. 

Dean sets down his food. “You really can’t be this clueless. I get it, you were playing to my strengths and all, letting me teach you about the shit I like, but you can drop it. You win, okay?”

“I win?” Cas echoes, bewildered. 

“Yeah, ha ha, you got me,” Dean mutters before he crams his cakehole with pizza.

“I don’t understand.”

Dean stares him down as he chews, his gaze raking over Cas’s face for a tell, a twitch, anything that’ll give the game away.

Cas stares guilelessly back. 

Dean huffs and turns back to his soap.

“Dean?”

Dean shoves the rest of his slice in his mouth in three impressive and slightly nauseating bites. He swallows with effort. “Think I’m gonna turn in. Early morning tomorrow, with lots of grovelling ahead. Gotta get my beauty sleep.”

“But-”

“See ya in the morning,” Dean says before he hightails it out of the living room. He closes the door behind him and sinks down on the bed.

Huh, Cas wasn’t lying about the memory foam.

* * *

Michael slinks into Crowley’s office at eight o'clock on the dot. He hands Crowley his morning cappuccino and takes a step back, head bowed and hands clasped in front of him like a man standing before the gallows.

“Nice of you to show up,” Crowley says, making no move to take the drink.

“I’m sorry, sir.”

“I should hope so,” Crowley sniffs, and probably nobody but Michael could discern the hurt in his voice. “You never texted, never called. I was about to send out a bloody search party for my wayward assistant. Do you know how many yuppies would kill for your position?”

Michael cringes as he takes a seat. “I'm sorry, sir,” he repeats, his voice barely above a whisper.

Crowley leans back in his seat. Fingers steepled, he asks with a put-upon sigh, “Now, tell me, Smith. What was so goddamn important yesterday you had to miss work without a word?”

Michael scoots forward in his seat. “I was with the police,” he says, his face unbearably earnest. “They wanted me for questioning about a robbery.”

Crowley's eyes widen as he puts the pieces together. “A robbery,” he echoes faintly.

“I-” Michael falters, “They said someone had stolen a large amount of money from your house? And since I am close to,” he coughs, looking away, “you, they said I was a suspect. I’m your most recent employee, so…”

Crowley scowls. "You were with me the whole damn weekend.”

“The LAPD thought I knew something.”

“What a bunch of morons.”

Michael licks his lips. _“You_ don’t think I had anything to do with it, do you?”

“Of course not,” Crowley scoffs. 

Michel exhales a relieved breath, deflating like a popped balloon. “I’m so glad, sir.”

Crowley reaches for his cappuccino and takes a sip. “About last weekend, though,” he starts. 

Michael snaps to attention. “Sir?”

“I briefly considered - erroneously, obviously - you were having second thoughts after the night we spent together,” Crowley says in a low voice.

Michael shakes his head vigorously. _“No,_ sir. Nothing of the sort. I - I actually enjoyed myself very much.” He ducks his head, staring at his hands.

Crowley swallows, his fingers tapping against the side of his cappuccino nervously. “Good. I’m glad to hear that - not that I thought differently, mind.”

Michael’s eyes dance with mirth. “Of course not, sir.”

“Cheeky,” Crowley murmurs over the rim of his drink. “Are you free on Saturday evening?”

“Yes.” Michael doesn’t hesitate.

Crowley’s mouth stretches into a wide, satisfied smile. “I will pick you up at seven.”

Michael stands, pausing in the doorway. “Oh, sir, I’ve moved.”

“You have?” Crowley asks.

“A main pipe broke in the apartment above mine,” Michael explains. “I needed to relocate while they fix the water damage to the floors.”

“Text me your new address,” Crowley dismisses with a wave of his hand.

“Yes, sir, right away,” Michael says with a small smile before he slips out the door.

He takes a seat behind his desk, waving to Ruby as she passes by on her way to Abbadon’s old office, now occupied by junior partner Asta Roth. She ignores him, which Michael expected. He did get her boss fired, after all, even though there’s no paper trail that links directly back to him.

He wakes his computer back up, tapping impatiently on the space bar as the screen hums to life and notifications pop up one after another. With a heavy sigh, Michael gets to work.

His first interruption comes a little after lunch. With a furtive glance around him, he pulls out his fancy new FBI phone. It’s fancy ’cause the Agents have full access to all its data, and Charlie’s number is blocked. Which isn’t to say she can’t get her hands on a new phone and get in touch, but since she's at her own safe house in South Dakota, complete with FBI handler, he doesn't expect to hear from her for at least a week.

 _Cas 12:58_ _  
__What time should I pick you up after work?_

 _Dean 1:00_ _  
__I’ll probably be out by 7:30_

 _Cas 1:00_ _  
__I will wait outside your old apartment._

 _Dean 1:04_ _  
__For debrief?_

 _Cas 1:04_ _  
__Yes. Where are the photos? I will get them before you arrive._

Dean stares at Cas’s latest message for a full minute, his gut churning unpleasantly as doubts cloud his head like an incoming thunderstorm. He has got to remember: Cas could still pull a dick move, reveal himself as a wolf in a sheep’s fugly trench coat. Sure, Cas told the truth about his brother and his stupid car, but Dean can’t take anything else for granted. Not again.

Who knows what Cas wants with that kind of leverage.

 _Dean 1:10_ _  
__It’s fine. Forget them._

Cas’s typing dots pop up before Dean can even put his phone back in his suit pocket. 

_Cas 1:10_ _  
__It will be immeasurably more difficult to find them if you don’t give me a precise location._

 _Dean 1:10_ _  
__Then don’t bother._

The dots appear, disappear, and appear again, longer this time, before disappearing.

Michael gets back to work, gritting his teeth as Crowley gets into a screaming match with Gerald from accounting over the Roman account.

* * *

The photos are waiting on Cas’s dashboard as Dean gets into the Lincoln. He stares at them for a few seconds, jaw clenched and more confused than ever. He stuffs them in the pocket of his jacket before Cas can snatch them back.

Cas starts the car. “How was work?”

“Shouldn’t we wait for Agent Ginger and Agent Limey before we debrief?” Dean asks, eyebrows raised.

Cas frowns. “This isn’t a debrief,” he says as he pulls out onto the main highway. “I was just making conversation.”

“Why?”

Cas frowns, his brow furrowing as he answers Dean’s question, “Because that is what two people do when in a car together? We could sit in silence, but I’ve been told it makes people uncomfortable.”

The awkward loner act strikes again. Dean's got to give Cas credit, the son of a bitch commits to the role even past curtain call.

“You’ve been told, huh?” Dean asks, his tone dripping with skepticism. 

“I personally have no issue with it,” Cas says, as he turns on his blinker a full five seconds before he switches lanes.

So Dean tests him. They don’t speak for the rest of the drive, and Cas only shoots Dean about two dozen odd glances the whole way.

Debriefing is relatively painless but definitely less fun than with Charlie and Jo. He reports on his next date with Crowley and passes over a flash drive containing most of Crowley’s financial reports from the past two years.

When they let him go at around nine, Dean stands because everyone else is leaving, but not with any real clue where to go.

“Dean?” Cas asks, waiting in the doorway. “Is something wrong?”

Dean shrugs. “Not sure what I’m supposed to do next.”

“I imagine resting up for tomorrow,” Cas says with a small, one-shouldered shrug. “Isn’t that what most people do on work nights?” He tilts his head towards the hallway. “Are you coming? I believe we covered everything during the meeting.”

“Uh, yeah,” Dean says as he beats a hasty exit after Cas. “I’m right behind you.”

Dumbly, he follows Cas down the hallway, into the elevator, and out to the parking garage. He gets into Cas’s ugly-ass Lincoln, and waits as Cas silently drives the short commute back to his apartment.

Back inside Cas’s living room, he pauses. “Is this going to be a thing now?”

Cas pokes his head out of his bedroom, his tie lying half-untied around his neck. “I’m sorry, I know how much you love your car. But unfortunately, you must have a detail at all times, including to and from both our workplaces.” He smiles wryly. “And I don’t think you trust me enough to drive your car for you.”

 _“No,”_ Dean barks forcefully.

Cas takes a step back, hands up in a gesture of no-harm. “I understand.”

Dean shakes his head. “But I wasn’t talking about the transport, I meant my staying here. This gonna be a permanent thing?”

Cas pulls the rest of his tie free, fingers clenching around the fabric. “It is, unless you would prefer to stay with a different supervisor.”

“I thought you’d sic some junior agent on me,” Dean says in a faux-causal sort of voice. “Babysitting is a bit below your paygrade, isn’t it?”

Cas looks up, his blue eyes wide. His tie hangs limply from one hand. “You are our most valuable asset in the Lightman case. Ensuring your safety is one of my utmost priorities.”

Dean swallows. “You must be tired of my ugly mug by now.”

Cas shakes his head, completely shameless.

“Right,” Dean says, a little unsettled. No normal person with a normal agenda would just up and _admit_ that. What the hell is Cas up to?

Dean jerks his head towards his bedroom door. “Okaaay,” he says, drawing the syllables out, “I'm gonna-”

“Do you want to watch Jeopardy!?” Cas asks out of nowhere.

Dean pulls out his phone to check the time. “Jeopardy! was like three hours ago, dude. Unless you're talking about some rerun.”

“I recorded it.”

“You what? Why?”

“You said you watched it every night, barring other plans,” Cas says, and he sounds honest to god nervous. “I thought you might want to see it tonight, given all the recent upheaval in your schedule.”

“I - yeah, sure,” Dean stutters, unable to say anything else in the face of Cas's expectant stare. “How’d you know I did that?”

“You told me.”

“When?”

Dean has the feeling they’ll be having this conversation a lot.

“Last week,” Cas says as he walks past Dean, who’s still rooted to the spot, and picks up the remote by the television. “We were waiting in line, and you were talking about how you already missed Jeopardy! twice that week already because of late work hours.”

“Right,” Dean says as he weakly drops himself onto the couch, leaving a full cushion of space between him and Cas. “That sounds like me.”

Cas nods once before he turns on the television. 

The first contestant goes for BEE LIST STARS for one thousand. 

Cas rattles off the answer, “Bee bread,” before Alex finishes the question. 

“How'd you know that?” Dean asks, dumbfounded. 

“I told you, I like bees,” Cas says defensively before flapping a hand in Dean's direction for him to be quiet. 

The contestant goes for Bee again, for eight hundred. 

Again, Cas answers: the process of preparing for a new bee colony. “Swarming.”

Six hundred takes a beat to register with Cas. As the contestant flubs the first word, Cas guesses, “Flight of the Bumblebee.”

The next contestant also chooses Bee.

Cas answers each and every Bee question correctly all the up to the easiest two hundred clue: “Bumblebee is a member of this alien race, locked in battle with the evil Decepticons.”

After Cas sits in stumped silence for a split second, Dean takes pity on him. “They’re Transformers,” he says at the same time as the contestant.

Cas frowns. “That has nothing to do with bees.”

Dean stares at him in disbelief. How many of those movies have there been? Three? Five? Ten? Not to mention all the toys. There’s no fucking way Cas didn’t know the easiest clue in the category.

“You seriously-” Dean starts, but Cas cuts him off with a very librarian-esque, _“Shh!”_

“The Good Samaritan,” Cas gets correctly again, and they’re moved onto BIBLE STUDY. “Herod,” Cas says next. “Deuteronomy,” then, “Death, war, famine, and pestilence.” He snorts as the next clue comes up, muttering, “The Archangel Gabriel.”

The next contestant finally moves on from Bible Study, and instead chooses FAMOUS RECLUSES for one thousand.

“Salinger!” Dean blurts as Trebek reads the first question.

“Emily Dickinson,” Cas guesses for the next one.

“Come on, of course it’s George Harrison.”

“Isaac Newton.”

“Bobby Fischer, I think?”

Before they get to the last clue, the contestant switches categories to ISLAND NATIONS.

They only get through one question neither Cas nor Dean know the answer to before they hit the first commercial break. 

“So, you know your Bible,” Dean says, turning to Cas.

Cas shrugs. “I went to a Catholic boarding school. We had a religious requirement every year.” He smiles wryly. “The nuns made sure their lessons did not fade with time.”

Dean blinks. So Cas really did go to boarding school?

“And Stanford after that?” Dean guesses, half-hoping to catch another one of Cas’s lies.

But Cas nods. “After Stanford, a few tours in the army, and then the FBI.” He sighs with a dark look, “The family business.”

Dean gapes, incredulous. “The FBI is _the family business?”_

“Of course it is,” Cas says like it’s obvious. “I have about twenty relatives working in some way or another with the Bureau. Anna is actually my fourth-cousin.”

If Cas likes bees, has a brother who fucked up his car, attended boarding school, went to Stanford, and works for the family business - did he actually lie about anything?

Or is he lying about all of it? Carrying on the charade for some increasingly convoluted endgame?

Dean leans back and tries to relax even as his mind races with possibilities. He hardly watches the ad for Herpexia.

Fool Dean once, that’s on him. 

Fool Dean twice... and that’s apparently on him too, because he’s starting to believe Cas is exactly who he said he was.


	6. The Convincer

**Summary for the Chapter:**

> Cas’s jaw clenches. “I wasn’t trained in any of this, the deception, the manipulation-”
> 
> Dean cuts him off with a derisive laugh. “Good for you. You must be a natural.”
> 
> Cas’s eyes flash dangerously. “I am not.”
> 
> “Bullshit.”
> 
> “It is not bullshit,” Cas hisses, and Dean’s eyes widen at the swear. “Do you know what is bullshit? When you chose _me_ in the first place!”

The next few days pass in the same manner. Cas drives Dean to work. Michael flirts with Crowley. Dean debriefs the FBI. Cas and Dean head back to Cas’s place and watch Jeopardy! or Dr. Sexy, MD. Cas works overtime from home. Dean goes to bed. Cas (probably) goes to bed. Jury's still out on that one, since Cas is always awake before Dean gets up in the morning. 

But despite all the time they spend together, Dean still can’t figure him out.

One early morning, Dean snoops through Cas’s mail and conducts an in-depth perusal of his living room for personal items. Apart from a truly embarrassing set of dust-covered yearbooks from Edlund's Preparatory Academy (Senior year, Cas was voted Most Likely to Take Over the World - _did his classmates know him at all?)_ nothing verifies any of Dean's suspicions. 

Saturday breaks up his routine in the most unpleasant way possible. Crowley has his driver pick Michael up, and they have a romantic catered dinner at his sprawling house in the Hills. 

Dean pulls out the roofies again. This time, he gets away by the skin of his teeth. Crowley’s dogs sense something is amiss and bark their heads off. Fucking narcs. Luckily, Crowley is still conscious enough to call them off and send them outside.

On Sunday, Dean resolves to get to the bottom of the whole Cas mystery. He's going to pull out the big guns: a home cooked meal. So far, Dean has only seen Cas eat food from a takeout bag or the FBI cafeteria. Dude’s gotta be itching for real food.

When Dean brings the meal up to Cas, he explains it as, “a thank you for letting me crash at your place.”

Cas is surprisingly unreceptive to the idea. He squints harder at Dean. “You don't have to thank me.”

“Fine, then, an opportunity to get to know the real you,” Dean says, his tone a bit more accusatory than necessary.

“You already know me,” Cas says, his confusion deepening. “We spent a considerable amount of time together, even before you moved in.”

“No, no,” Dean says quickly. “I knew boring accountant Cas, not the _real you.”_

Cas says coldly, “That was me.”

Dean forces an easygoing smile on his face. “I’m not talking about the fake-you you put on to get close to me.”

“There is no ‘fake me’,” Cas says, finger quotes and everything.

Dean barely resists rolling his eyes. What a stubborn son of a bitch. “You expect me to believe that,” he waves up and down Cas’s body, “the baby in a trench coat who doesn’t know the difference between the Death Star and Dancing with the Stars is the real deal?”

“Yes.”

“You can’t be serious.”

“Of course I am.” Cas’s jaw clenches. “I wasn’t trained in any of this, the deception, the manipulation-”

Dean cuts him off with a derisive laugh. “Good for you. You must be a natural.”

Cas’s eyes flash dangerously. “I am not.”

“Bullshit.”

“It is not _bullshit,”_ Cas hisses, and Dean’s eyes widen at the swear. “Do you know what is bullshit? When you chose _me_ in the first place!”

Dean draws a blank. “What are you talking about?”

“I'm talking about that first day - when we met,” Cas growls, his voice growing more heated by the word. “Agent Milton and Agent Balthazar were both there. You were _supposed_ to fall for one of them. _Not me._ My position is in corporate white collar crime. I - I - I investigate spreadsheets and tax returns! If I have to - if no one else from my team is available - I pose as a client or a systems inspector. _That is it.”_

Dean’s throat dries up faster than the Sahara, taking his retort along with it.

“I was only there for backup,” Cas continues sharply. “I was supposed to stand there, receive my orders from Anna, and go back to the office when you got her number. Instead, you spoke to me.” The corners of his mouth tighten. “You wanted _me_.”

Dean stares, completely dumbfounded.

Cas adds, his voice sardonically dour, “You remember, I even asked your advice about what to do.”

“You did?”

Cas throws him a pitying look. “I asked you how to deal with a client I needed to like me. Balthazar later said I was about as subtle as the Titanic.”

“Oh,” is all Dean can manage. For once, he does recall _that_ conversation in the coffee shop.

Cas sags in his seat. He rubs a tired hand down his chin. “And now you think I’m some sort of - sort of _Mastermind of Duplicity.”_

“I,” Dean starts without any real idea how to end his sentence, “didn’t really think that,” he says, not entirely truthfully. He sure doesn’t think that _now_ , since no self-respecting con man would ever call himself a Mastermind of Duplicity. Not unless he wanted Sam to laugh him off the face of the Earth.

Cas glares, his eyes steely. “You’re usually a better liar, Dean.”

“Okay,” Dean starts, “maybe a small part of me wondered. But not seriously. To keep up the con for that long, past the whole FBI reveal, I didn’t get it, you know? Just - why?”

Cas’s brow furrows. “I don’t know. None of this makes sense to me.”

Dean chuckles. “That makes two of us.” He sneaks another glance at Cas, dressed casually for the weekend in a pair of jeans and one of those white tee shirts that come in packs of six from a department store. “Now what?”

Cas gestures to the door. “You mentioned needing to get groceries.”

“You still wanna go?”

Cas blinks, surprised by the question. “I suppose? If you’d rather do something else, I can get food delivered tomorrow instead.”

“No, let’s go,” Dean says quickly as he ducks down to put on his shoes. “I think I need some fresh air.” 

In the Lincoln, Dean lets Cas get comfortable behind the wheel for five minutes before he blurts, “You really didn’t know about Transformers?”

Cas shoots him a confused look. “The aliens who battle Decepticons?”

Dean snorts at the near verbatim Jeopardy! question. “Yeah, that’s them.”

Cas shakes his head. “I have heard the term in passing, maybe? I did not know one of them was named Bumblebee, which was the essential part of the question.”

“Star Wars?” Dean tries next.

“Only the movies-”

“Episodes.”

“-Episodes,” Cas corrects with an eye roll, “we watched together.”

“Harry Potter.”

“They were considered anti-Christian and banned from my high school. I am aware of the basic plot.”

Dean whistles. “You could’ve read them later.”

“I had little interest by that point.”

“Star Trek.”

“Is that different from Star Wars?”

Dean gapes. “Dude.”

Cas pulls into the parking lot of a Trader Joe’s. “What?”

“Kirk? Spock? Beam me up Scotty?” Dean tries with increasing desperation as he clambers out of the Lincoln.

Cas shakes his head.

“Finding Nemo.”

“Yes, I have seen Finding Nemo,” Cas says as the automatic doors open. “I took my niece to see it in theaters.”

“Bingo!” Dean says. “Wait, what niece?”

“Gabriel’s daughter,” Cas explains. “He needed her out of the house when he catered Thanksgiving, so Kali and I took Ashika to the movies.”

“You didn’t stay and peel potatoes?”

“I had enough of peeling potatoes in basic training,” Cas says darkly.

Dean grabs a basket for their groceries, and they wind their way through the store. He grabs an assortment of vegetables that would make Sam proud, ground beef, American cheese, hamburger buns - all the essentials, plus spices, since Dean didn’t see a spice rack in Cas’s kitchen last time he checked.

All the while, Cas bears Dean’s pop culture quizzing with a patiently amused smile.

As Dean piles groceries on the cashier’s conveyor belt, he prompts, “Magic Mike?”

“Does that also have to do with witches?” Cas asks totally straight-faced, and Dean has the strangest inkling Cas is messing with him.

“Close,” Dean says, playing along. “Strippers.”

Cas pulls out his wallet.

“Hey, no,” Dean says, jumping forward. “I got this. It was my idea.”

“While very kind of you to offer,” Cas says as the reader beeps angrily at him to remove his credit card, “I can expense this purchase to the Bureau if it goes towards feeding or housing you.”

“Awesome,” Dean says with a wide grin. “Glad to see my good tax dollars at work.”

Cas throws him a wry look. “You have never paid federal income tax in your life.” He hefts grocery bags into his arms. “Don’t try to convince me otherwise.”

* * *

“You like ‘em rare, right?” Dean calls over his shoulder.

Cas appears at his elbow without a sound, and Dean barely refrains from stabbing him with the spatula. Cas nods.

“See, I remember shit too,” Dean huffs as he turns back to the patties browning in the pan.

Cas peers over Dean’s shoulder, asking, “Are you sure there’s nothing I can do to help?”

“For the last time, _no,”_ Dean says. He points the spatula at Cas’s chest. “Burgers are sacred, Cas. I don’t want you fucking it up. Chill - put your feet up a little. You remember how to do that, right?”

“Yes, because becoming a senior agent at the FBI was accomplished through copious amounts of relaxation,” Cas mutters as he walks back towards the living room.

“And don’t you dare touch that computer!” Dean orders. “I mean it - burgers’ll be ready in five. You won’t be able to get any work done ‘fore then.”

“Yes, Dean,” comes Cas’s grumble.

Dean hums Metallica as he slides the patties onto a waiting plate and toasts up the buns in the greasy pan. 

"Order up!" Dean says with a flourish as he deposits the burgers on the kitchen table. "I left 'em open faced so you can add whatever the hell you like."

"Thank you," Cas says sincerely as he carefully places a few leaves of lettuce, rings of onion, and a single tomato slice. He hesitates, his hand hovering over an open jar of pickle slices, and tentatively forks a couple out.

Dean watches avidly as Cas takes his first bite, his face going nirvana-levels of blissful.

“You like it?” Dean asks as he loads up his own burger.

“This is very good,” Cas says before daintily wiping his mouth with a paper towel. “Do you cook often?”

Dean shrugs. “Have to, in my line of work.”

“Have to?” Cas echoes, head tilting as he tries to parse out the meaning in Dean’s words.

“Ever heard, the way to a man’s heart is through his stomach?” Dean asks wryly.

Cas throws him a thoroughly unimpressed look. “I _am_ very widely read. I do not struggle with idioms, Dean - only pop culture references.”

Dean holds his hands up. “Just makin’ sure. Can’t be too careful.” He takes a huge bite of his own burger, swallows half, and keeps talking. “Nothing impresses a mark like a well cooked meal.”

Cas’s eyes flick down to his own burger, appraising.

“Wait!” Dean blurts, reddening deeper than the middle of his perfectly rare burger, “This isn’t like that. I’m not trying to get into your pants anymore.” He chuckles humorlessly and soldiers on, “I know where we stand. This is purely a thanks for putting up with me. That’s it.”

“Oh,” is all Cas says. He focuses on his food, tucking in stray bits of lettuce slowly slipping out the sides and reorienting the top bun so it aligns with the bottom.

“I mean it,” Deans says, since Cas has that squirrelly, uncomfortable look about him. “I’m not trying to get into your pants.” He smiles - a forced, wasted effort since Cas won’t look at him. “You don’t have to worry.”

“Right, of course,” Cas says stiffly.

Dean takes another huge bite of his burger as he tries to think of the least-subtle way to change the topic. It’s not like Dean doesn’t get it. Talking about old seductions always make him feel a little gross - remembering the touching, the intimacy, the sappy looks on their faces as they fell a little bit more in love with him.

It used to be a thrill, having that much power over someone else without the handicap of being in love back. No rose-colored glasses clouded Dean’s judgement as his marks fell over themselves to get close to him.

And before Cas, Dean could focus only on that. Not the drop when he inevitably had to leave everything behind. Dean would remember how nice it was to feel wanted, and he could push on to the next job. It was addictive; the attention, the idolization, the love, were all his drugs of choice.

Dean was king of the con before Cas.

Now what is he doing? Pushing through like a pro player past this prime.

“What kind of food would you cook for them?” Cas asks, still focusing on his burger like it holds the secrets of the universe.

“All kinds. I once spent a whole month perfecting beef wellington. Puff pastry was a bitch to make from scratch, lemme tell you.”

“I stopped using my kitchen after I set my toaster on fire.”

Dean doesn’t bother holding back a snort of laughter. “How the hell did that happen? You seem the type to follow the recipe to the letter, measuring and timing the fuck out of everything.”

Cas’s brow furrows. “Do _you_ not measure out ingredients or use a timer?”

Dean see-saws his burger-free hand back and forth. “Depends. If it’s complicated and my first time doing it, yeah. Otherwise, you gotta _feel it.”_

Cas’s mild frown deepens. “I don’t understand.”

Dean takes a sip of water before he explains, “Cooking is as much an art as a science. You can treat recipes more like guidelines once you get the basics down - you can mess with ‘em a ton and still get good food out of the end.”

“From what I’ve seen, that is how Gabriel cooks,” Cas admits

“I mean, don’t experiment too much,” Dean warns, “fluff marshmallow mix and macaroni _do not_ mix.” He shudders. “Trust me.”

Cas recoils in disgust, before asking tentatively, “Where did you find a recipe that combined pasta and marshmallows?” 

“Oh, that was a Dean Winchester original,” Dean says with a laugh. “Sammy wanted something different in his mac and cheese, and marshmallow fluff was all we had left.”

“That sounds disgusting.”

“It was,” Dean says with a grin. “But that’s what happens when you have two bucks to your name and another week at the Royale Motel in Scranton.”

Cas’s eyes widen. He opens his mouth, probably to ask a bunch of questions in that uncomfortably direct way of his, but Dean cuts him off before Cas can begin. “Anyway, I wasn’t a genius like Sam, but I could be inventive when I wanted to be.” He squirts more ketchup on his burger. He has to be careful about it, or he could end up with half the bottle spilling on his hand.

“Yes, I’ve seen that for myself,” Cas says quietly.

Dean crams more burger into his mouth, leaving no room for words.

“I never had the occasion to learn,” Cas says, wiping his hands on his napkin. “My family always employed cooks, and then in high school we had a cafeteria.”

“College?”

“I was on a meal plan,” Cas admits, ducking his head. “In the military I picked up some skills, but I hardly ever have the need to feed a whole platoon anymore,” he says with a small smile.

“And now here you are,” Dean says as he gestures at Cas with the remains of his burger, “a fully grown man who set his toaster on fire.”

Cas wrinkles his nose. “It was an old toaster, if that redeems me at all.”

“Next, you’ll be telling me you don’t know how to use a waffle iron.”

“Why?” Cas asks, head tilting. “Is it difficult?”

* * *

Dean can appreciate the ballet. The dancers, both genders, are usually super hot and able to do crazy cool things with their bodies. 

He fucking loves the movies - Westerns are the best, but Dean would never turn down a good sci-fi or action flick.

Theater, yeah, sure, Dean can get behind it. From one actor to another, he can always appreciate a good performance.

Opera, though, Dean _does not understand._

First, it’s always in a different fucking language. Dean can read subtitles; _that’s not the issue, Sam._ But he can never figure out if he should be looking at the words or the singers.

Second, the music _sucks._ Someone should write a catchy opera. They’d make a goddamn killing. Bits and pieces are okay, but the songs are usually an orchestra arrangement of rambling.

Third, everyone dies at the end. In. Every. Single. One. Talk about repetitive. There should at least be more explosions. Or beheadings like in Game of Thrones.

Dean has better things to do with _four-and-a-fucking-half hours_ of his life. Namely, anything else.

For this, Crowley’s not gonna enjoy fake sex tonight.

At least Crowley seems pretty into it. He keeps leaning over to whisper something in the ear of their double-date partner - one of their clients, Monroe Styne.

Stynes’s wife seems equally enthused about the performance, her gaze riveted by the stage for the past two hours.

The action finally breaks an hour later, and Dean's the first to his feet to stretch his cramped legs. 

“Michael,” Crowley says warmly, “How are you liking the performance?”

Michael says brightly, “I really see what the critics are saying. The soprano was really an inspired choice for Juliette. She’s a standout.”

Monroe harrumphs. “Sure, she can sing. But she doesn’t really _fit_ the part, does she?”

Michael shrugs. “I think she fits the part just fine,” he says coolly. 

Juliette looks a lot like one of Dean’s old marks, one of his earliest ones. Cassie Robinson’s family had to sell their car dealerships when Dean left them with nothing after the elopement.

Dean would bet his baby Styne’s idea of ‘fitting the part’ has nothing to do with charisma or vocal talents. Styne’s eyes narrowed every time Juliette and the white tenor cast as Roméo touched hands.

Crowley glances between the two of them, eyebrows raised. “Why don’t we get some refreshments?” 

Michael gives him a small nod, and they make their way out of the box.

“Dreadful stuff,” Crowley says, not bothering to lower his voice. “It’s a bit like stabbing myself in the ear with a dull cleaver, but it’s what you do for clients.” He elbows his way towards the front of the drinks line and raps his knuckles on the bar. “A scotch,” he says, “And one more for my friend, here.”

Michael ignores the glares from all the people Crowley cut in line and instead focuses on his mark. “You’re not a fan?”

Crowley hands over his card to the bartender and takes one of the glasses in hand, draining half of it in one go. “I’m a simple man, Michael,” Crowley sighs. “Grew up dirt poor in the arse end of Scotland. Made my way to America, yadda, yadda, yadda. Long story short, becoming the fifth richest man on the West Coast wasn’t easy. Sometimes it required - to borrow a phrase from the US military - _enhanced_ techniques, if you catch my drift.”

Michael takes a careful sip of scotch before saying, “I think I do, sir.”

Crowley casts him one long, assessing look. “I think you do too,” he says quietly. “Anyway, this is hardly the worst of it.” He waves his hand to indicate the elaborate hall around them. “In fact, many people would consider this a perk of a job well done. Remind me to tell you about what happened to Pendleton.”

Michael dips his head. “Yes, sir.”

* * *

Dean should know better than to play with fire. But, as predictable as losing a land war in Asia, he can’t help himself. So that’s how he finds himself next Sunday morning teaching Cas how to make a proper breakfast. 

“Lumps are fine,” Dean says as he wrests the bowl out of Cas’s hands before he can mix the batter into an oblivion.

Cas throws him an accusatory look. “That can’t be right.”

“Who’s the expert here, you or me?” Dean asks, eyebrows raised.

“You,” Cas mutters, defeated.

“Got that right. Is the bacon done?”

Cas hums his assent as he lifts the cooked bacon out of the frying pan and onto a waiting plate covered with a paper towel.

“Awesome,” Dean says as he leans over to inspect Cas’s work. “Here,” he says as he nudges an empty mug closer to the bacon plate. “Pour the extra grease in here.”

Obediently Cas does as he’s told, and Dean gives the batter one last stir when Cas looks the other way. “See,” he says, grabbing Cas’s attention before pouring out the first pancake. “Not that hard.”

Cas looks on, his face doubtful. “It’s not shaped like a normal pancake.”

“What are you, the breakfast police?” Dean demands as he sets the bowl down. “The first one is always fucked up.”

“Why?”

Dean shrugs. “Something to do with the oil in the pan or something? I’m not sure. I’ll eat this one, anyway. Doesn’t matter.”

Cas eyes the half-cooked pancake speculatively. “May I make the second one?”

“I was counting on it,” Dean says with a grin. “Teach a man to fish, and all.”

“I don’t think I can survive on pancakes alone,” Cas says skeptically.

“That’s why we made bacon too,” Dean says wisely. He points at the pancake. “Look, the bubbles there? It’s ready to flip. You wanna do the honors?”

Cas’s face settles into a determined expression. He looks like he’s gearing up to take on the Imperial Army as he takes the spatula in a vice-like grip.

“Hey, no,” Dean gently takes Cas’s elbow in hand, “You gotta loosen up. You don’t want you flipping this thing onto the ceiling. Believe me, it’s a bitch to scrape off.” At Cas’s curious look, Dean rolls his eyes. “Wasn’t me. Sammy got a bit too enthusiastic his first time too.” He snorts. “Poor guy can’t cook for shit either.”

“You never taught him?” Cas asks curiously.

“Pancake’s gonna burn, Cas,” Dean reminds him gruffly. “Here,” he says, sliding his hand down Cas’s arm to grip his wrist. He demonstrates the necessary flipping motion. “Like that,” he finishes before stepping away to open Cas’s tiny fridge. He grabs the carton of orange juice, lingering a little too long to cool his heated face.

“Shit,” Cas murmurs behind him.

Dean strides back over to the stove, unable to help his laughter. Half the pancake ended back in the pan, half dripped over the sides, almost onto the burner.

“It’s fine,” Dean gently nudges Cas out of the way to fix the damage. He slides the pancake back in, doing his best to hem in the uneven edges. “Not bad for your first time. I’ll eat this one too.”

“You’ll eat all of them at this rate,” Cas grumbles as he pours out the orange juice into two glasses. 

“I’m not complaining. I love pancakes.”

Cas smiles, a small barely-there thing Dean barely catches before Cas turns away to get out silverware and plates.

“You wanna try the next one?” Dean asks. “I promise I won’t eat it, no matter how it turns out.”

Cas appears at his side like a ghost. “I will try again.”

“Alright,” Dean says as he flips the finished pancake out of the pan and onto the plate. He watches intently as Cas pours in the next batch of batter. Cas’s eagle eyes rove around the mostly-circular surface, probably looking for those telltale bubbles.

“Until you fuck up a whole breakfast shift’s worth of pancakes,” Dean says, “you won’t beat the worst cook out there. Beats me how that kid got the job in the first place. You should’ve seen him, sweating bullets at the griddle with the whole waitstaff breathing down his neck.”

Cas’s gaze flicks up briefly to meet Dean’s. “Which con were you running at that time?”

“Uh, none,” Dean says, eyes downcast. “It was back in high school, actually. I had a job as a dishwasher, and I worked my way up to waiter before we had to leave. Worst morning shift ever.”

“I’m sorry,” Cas says as he turns to face Dean fully, his blue eyes wide. “I shouldn’t have assumed.”

“No, assume away,” Dean says in a would-be casual tone. “It’s been my life for the past ten years and change.”

“You did say you liked working with your hands,” Cas points out. “That can’t have started when you met Lightman.”

Heat flares in Dean’s cheeks. “It didn’t,” he mutters.

“When did you discover you liked doing things like this?” Cas asks curiously.

“Not sure,” Dean hedges. “Dad let me help out whenever he was working on the Impala. Now I think about it, all I did was hand him stuff and tighten a few bolts, but it still felt important, you know? She was practically our home since we moved around so much. Getting her runnin’ in top shape, hearin’ her purr made me feel good.”

“You like seeing the positive results of your work first-hand,” Cas surmises. 

Cas doesn’t say anything about Dad, but he probably gleaned about a dozen facts from that one tidbit. “Yeah, I guess,” Dean says quietly. He points to the pan. “That one’s ready to flip.”

“Oh, of course,” Cas says, flustered at the change in topic. “I don’t-” he starts before breaking off.

“Come on, a smart guy like you can flip a damn pancake on his own,” Dean chides even as he steps around Cas to hold his wrist like before. His whole front tingles where it’s pressed flush against Cas’s back, so Dean lets his mouth run to distract them both, “Okay, since you apparently need the baby steps version-”

“I am not a baby.”

“Sure you’re not,” Dean snorts as he guides Cas’s to nudge the spatula under the pancake. “Here, like this.” They flip it together, and it lands perfectly in the pan.

Cas quickly extricates himself from Dean’s hold. “Thank you, Dean,” he says without looking at him. “I just remembered I have work to do.”

“But... breakfast,” Dean reminds him stupidly.

“I -” Cas breaks off, running a hand through his hair anxiously. “Can you handle it today? We - I - we can try again tomorrow.”

“Uh, yeah, sure,” Dean says, his heart sinking as the embarrassment kicks in. “Go do your Fed thing. I’ll finish up here.”

Before Dean can finish speaking, Cas disappears into his room.

 _Too far._ Dean always takes things too far. Logically, he knows Cas is only housing him to help the investigation and flirting makes him uncomfortable. But Dean had to push the envelope, had to test his luck, had to see exactly where Cas drew the line in the sand.

Congratu-fucking-lations to Dean, he found it.

* * *

They settle into a more detached routine after. Dean occasionally teaches Cas more staple recipes - omelettes, roast chicken, a properly cooked steak - always from a safe distance away from Cas. It hardly matters anyway, since Dean spends more and more of his weekends with Crowley. Crowley even takes him on a vacation to the Caribbean, about a month after their first getaway to the vineyards. The gossip at the office reaches a fever pitch; Crowley never takes a whole week off from work.

Michael and Crowley have a grand time sipping cocktails on the beach and being waited on hand and foot. They return to the office on Monday, tanned and punch-drunk on each other.

Dean gets whisked off to the FBI first thing that night to debrief. Milton and Balthazar put him through the wringer, squeezing every last detail out of him. Dean nearly has to go full frontal in his retelling before they back off.

Red-faced and feeling very small, Dean sits in the interrogation room as the agents leave on a water break. Cas returns long before Milton and Balthazar, carrying a spare cup of water for Dean.

Dean takes it for something to occupy his hands. He isn’t particularly thirsty.

“It’s not going to be for much longer,” Cas says in a low voice. “I recorded the Jeopardy! you missed.”

Dean can’t even say how low watching Jeopardy! ranks on his to-do list. He runs a hand down his face, grimacing as the pads of his fingers catch on a slight sunburn on his forehead.

“It’s fine, Cas.”

“The pizza parlor might no longer be open, but perhaps we could have Chinese.”

“I’m fine.”

Cas’s eyes narrow, disbelieving. He swallows, eyes darting once towards the still open door before settling back on Dean’s face. “You keep saying that. I, uh, don’t think that word means what you think it means.”

Dean cracks a reluctant smile. “Was that a pop culture reference?”

“I rewatched the Princess Bride last week while you were gone,” Cas informs him. “Of all the movies we’ve watched, that is my favorite.”

Dean clutches his chest with both hands. “Not Star Wars? Blade Runner? Batman?”

Cas shakes his head.

Dean snorts. “You’re a sap. Tell you what, you gotta see the Fifth Element next. Should be right up your alley. Plus, it’s got Bruce Willis.”

“Bruce Willis?”

“Come on, man,” Dean complains, “Die Hard? Die Hard 2? A Good Day to Die Hard?”

Before Cas can say anything else, Agent Milton and Agent Balthazar re-enter the room. Cas sits back in his seat, and Dean clutches tighter at his untouched water.

“Where were we?” Milton asks pleasantly.

Dean reports the rest of his sordid details of the trip, noting the suspicious names Crowley mentioned and the leads worth looking into.

At long last, the Feds let Dean go for the night, and he and Cas pile into the Lincoln for the drive back to Cas’s place. Dean stays quiet for the commute, silently trying not to think about what he’s had to do over the past week.

“It’s a bit early to go to bed,” Cas observes when Dean heads straight for his bedroom door.

Dean shrugs. “I’m tired.”

Cas tilts his head. “I’m going to get some more work done, if you would like to join me.”

“Pretty sure all that stuff’s confidential.”

“Well, I would appreciate your input nonetheless,” Cas demurs.

Dean shakes his head. “Maybe next time, Cas.”

In his bedroom, he methodically strips and gets into his pajamas. He catches a brief glimpse of a messy head of hair above the back of the couch as he sneaks out to brush his teeth and take a piss. Back in the safety of his room, Dean lays down in bed and watches the clock tick closer to eight, eight ten, eight fifteen.

He rolls over, closes his eyes, and tries to sleep in his new position. He kicks at the blankets, freeing his feet. He counts forty-one sheep. He checks the clock: eight twenty-two. He piles another pillow under his head and refrains from looking at the clock again.

He rolls back over, lays his arms by his side, perfectly parallel.

 _Corpse pose, shavasana,_ his mind reminds him in Lisa Braeden’s voice. Breathe in for four seconds… hold it… breathe out.

She used do that during sex too, count his breaths for him as he tried not to come. She would laugh as she did it, like she couldn’t believe he found her so hot he’d blow his load immediately without an intervention.

Dean turns back over, curling into the fetal position.

Just last night, he’d slept like this with Crowley spooning from behind.

Dean sits up and stalks back into the living room before he can overthink it.

Cas sits where Dean last saw him, leaning up against the armrest with both legs stretched out along the length of the couch. He looks up as Dean approaches, a tentatively curious expression on his face. “Can’t sleep?”

Dean silently shakes his head. He bends down, lifting Cas’s feet so he can sit down at the other end of the couch. Cas makes as if to move his feet to the floor, but Dean keeps a firm grip, keeping them in his lap.

“It’s fine,” Dean says. “Stay there.”

Cas throws him a dubious look but before he can say anything else, Dean asks, “What’re you watching?”

Cas squints at the television. “I had put on the news, but I’m not sure what this is.” 

Dean turns forward, idly rubbing Cas’s feet as he tries to make sense of the soapy high school drama playing on screen. Why do they all have perfect hair for Calculus? Who has the time? Dean was too busy scrounging together money or hustling to perfect his hair gel technique. (He got it eventually, of course.)

Cas lets out a little moan.

Startled, Dean’s hands jump back from the arches of Cas’s feet. “Sorry,” he mutters, freezing in place. At Cas's equally surprised look he mutters, “Habit, you know.”

“Habit?” Cas repeats, his voice strangled.

Dean reddens as he deliberately keeps his gaze focused on the television, not daring to look Cas in the eye. “Everybody likes a foot rub.” 

Cas blinks. “You don’t have to.”

“I don’t mind.”

“I’m not one of your targets,” Cas says quietly, and Dean’s head whips around to stare at him. Cas adds, “You don’t have to _perform_ for me. I don’t expect any of that from you.”

The embarrassment sinks in as the eye contact continues. “It’s not like that,” he protests lamely. Nobody understands better than Dean how out-of-bounds Cas is now.

“Isn’t it?” Cas asks, eyebrows raised.

Dean swallows, his throat dry. “No, it’s not,” he says, with a little more conviction. He inhales a slow breath, trying to put his thoughts into an order that makes sense. “You’ve never asked why I’m so good at the con.”

“I assumed it was because of your good looks and natural charisma,” Cas deadpans. “And because you can be utterly shameless.”

Dean struggles not to look too pleased. He taps the back of Cas’s foot once for emphasis. “It’s ‘cause I _like_ making people feel good. I learned to cook because it made Sam happier to eat things that didn’t taste like crap. I learned to fix my car because she was the most important thing in the world to my dad.” He runs a feather-light finger along the inside of Cas’s ankle, and Cas shivers in response. “I learned to be the best in the sack so I could always show my partners a good time.”

Cas coughs, a light flush coloring his cheeks. He mumbles, “I still don’t see how that makes you a qualified con artist.”

“You ever wonder _how_ I do what I do?”

Cas’s eyes flash up to his. “Ever since I first met you.”

“It’s not a con,” Dean says simply. “You have to show that person a part of your true self, and find something in that person you can really, truly fall in love with. You have to care about them, at least a little. That’s the only way.”

“That can’t be -”

Dean cuts him off. “Come on, who’s the expert here?”

Cas sits up a little straighter, laser-focusing in on Dean’s face. “You’re part of the most successful operation in Lightman’s service.” He doesn’t mean it as a compliment. “You can’t honestly tell me it’s because you _care_ about your victims.”

Dean flinches at the word. “I do,” he says quietly. “I know you don’t believe it, probably never will. But I do.” He swallows and switches to the other foot, ducking his head to focus on pressing his thumbs into Cas’s arches. “Might also be why I want out even though I have the best record out there,” he chuckles, “or the worst, depending on how you look at it.”

Cas stays quiet for a moment, resettling his computer in his lap and typing the occasional word - not enough to be doing any real work.

“You got a taste of what it takes,” Dean says into the silence, “with me. It’s hard when you completely shut your real self out, isn’t it?” he asks rhetorically. “It’s only believable if it’s real.”

Cas stares.

Dean chuckles humorlessly. “But, hey, maybe you’re better at the game than me. Ever consider a career on the other side? You could make a killing with that ace poker face you’ve got there.”

Cas doesn’t answer at once. Eventually, he says, “No, never.”

Dean looks up, and he can’t read that expression on Cas’s face. “No, you wouldn’t,” Dean agrees quietly.

* * *

“Let’s talk the proposal,” Balthazar says.

Dean shakes his head violently. “It’s too soon.”

Milton’s mouth purses. “How do you know?”

“We haven’t hit the half-year mark,” Dean says easily. “Nobody at Crowley’s age with that many zeros in his bank account will say yes.” 

Milton scribbles a few notes on her legal pad. “We can give you two more months.”

Dean lets his hands fall palm-down on the table. “Seriously? Don’t you want to do this right?”

“We don’t have unlimited resources,” Milton says, her expression serious. “We’re on track to go over budget and we’re already behind schedule.” She side-eyes Cas hard. “If you want your deal, you play by our rules.”

Dean scrunches up his face. “Are we talkin’ eight weeks until proposal or eight weeks until wedding?”

“Eight for proposal,” Cas assures him before Milton can get the words out. He glances down his notes. “One more month for the wedding.”

Milton shoots him a warning look. Cas placidly ignores her.

Dean runs a hand down his face, staring at the three agents sitting at the table. “You’re all nuts. I’ve never pulled off the con that fast.”

Balthazar purses his lips. “Reassuring,” he deadpans.

Milton runs a hand through her hair, glances at her two colleagues, and turns back to Dean. “What do you need to speed the process along?”

He exhales a slow breath as his brain runs through scenario after scenario that would force Michael and Crowley to get closer in a short timespan. 

Michael needs a green card to stay in the country? No, Michael would have asked for a work visa with his job application.

Stuck together in the office or elevator? No, a couple of hours together or an extra night wouldn’t be enough.

Meeting the in-laws? Dean already shot Michael in the foot with that one, since he told Crowley they were both dead.

Crowley needed a sign Michael was committed to the relationship. Tangible proof of Michael’s feelings for him. A promise of a future together.

“I need a dog.”

Balthazar does a double-take. “A what now?”

“A dog,” Dean repeats. “A puppy would be best. It has to be a Cane Corso.”

Milton taps a couple times on her tablet, eyes widening. “They cost more than a thousand dollars.”

Dean makes a face. “We’ll skimp on fancy wedding napkins and flower arrangements.”

Cas tilts his head, squinting at Dean like he can parse out his thought process if only he maintains eye contact for long enough. “Why do you need a puppy?”

Dean grins. “Who doesn’t like puppies?”

“Me,” Balthazar says with a grimace. “Dirty little things. Always shitting and yapping.”

Dean tuts under his breath. “And I thought you G-Men were stone cold before.”

Cas braces his elbows, learning closer over the table. “Why, Dean?”

Dean licks his lips. “I have to convince Crowley I’m here to stay and I want to be in his life for the foreseeable future. What says that better than raising a dog together? Second only to a kid, for a lot of people. Plus, Crowley already has one of those. He likes his dogs better.”

“You have two months,” Milton reminds him.

Dean sits back in his seat. “Then it better be a damn good dog.”

* * *

“I told you, we don’t have to keep him _here,”_ Dean says as he scrubs away at a corner of the carpet in his room. The cleaning agent tickles his nose, but Dean ignores it. He can only see Cas’s shiny fed shoes in the corner of his vision, but he can practically feel the glower Cas is undoubtedly directing at the back of his neck.

“It would be a greater hassle for you to move to be with the dog,” Cas says in a long-suffering voice.

Dean hums his assent. “Seems like obedience school is working. It’s what, his only accident this week?”

“So far,” Cas says sourly. “It’s still early.”

Dean straightens, grinning up at Cas. “Aw, I know you’re a big softie.”

Cas hefts the wriggling puppy into a more secure hold in his arms. “I always pictured myself owning guinea pigs,” he says dispassionately.

Dean reaches out with the hand not holding a paper towel soaked in bleach and dog pee to pet the puppy’s wrinkled forehead. “Come on, like you’d trade this little guy for a _guinea pig.”_

“The guinea pig is a noble creature, Dean,” Cas says stiffly, like Dean just insulted his mother. 

Dean barely stops himself from laughing. “I totally believe you.”

Glaring, Cas trails Dean out of his bedroom. He hovers in the doorway of the bathroom as Dean stashes the bleach in a cabinet and washes his hands.

Dean turns around. “Have you come up with a name for him yet? We can’t keep calling him ‘hey you.’”

Cas’s eyes flick down to the puppy in his arms, his expression softening for a split second. “A name would indicate familiarity.”

“I mean, the guy pees on your stuff,” Dean points out. “That’s pretty familiar territory.” He snorts. “It’s further than I ever let a chick get with me.”

“Thank you for that insight into your sex life,” Cas says flatly. He bends down and gently lets the dog go. “Truly, you live a thrilling existence.”

The puppy doesn’t go anywhere far. He plops right down between Cas’s feet and stares up at Cas, fuzzy forehead furrowed and eyes huge. The resemblance to Sam is uncanny.

Dean doesn’t blame the dog. If he could get away with pleading for Cas’s hands all over him every hour of the day, he’d do it in a heartbeat.

“A name, Cas?” he prompts.

“Shouldn’t you name him?” Cas volleys back, a little testy. “You are the one who asked for a dog and will be taking care of him after… after he leaves here.”

Dean bites his lip. “Yeah but…” he trails off, unable to voice how similar his feelings are to Cas’s - that naming the dog would mean he is getting attached. And who knows what his post-FBI life can include, or if he’ll have one at all. 

Cas shakes his head. “Crowley should pick. He’s his present, after all.”

Cas glares down at their new four-legged roommate, hands on his hips. With a long drawn-out sigh, he bends down and picks the dog back up. His face doesn’t so much as twitch as the dog enthusiastically sniffs his face and licks his nose. 

“Are you gonna be okay with him all by yourself tomorrow?” Dean asks as he heads back into his bedroom and goes back to packing for his sleepover at Crowley’s.

“He’s a dog, not a human infant.”

“Have you ever cared for a _human infant_ before?” Dean asks even though he can already guess at the answer.

Cas doesn’t speak. 

Dean raises his eyebrows, expectant. 

Eventually Cas says, mulishly, “No.”

Dean snorts. “Then I don’t know why you’re using babies as a frame of reference.” He throws in the extra large shirt he’s been wearing to sleep for the past week and plans to ‘forget’ at Crowley’s place. “They both eat, shit, and cry. At least puppies are cute.”

“And babies aren’t?”

Dean shrugs. “Some of ‘em. I’ve met a lot of ugly babies, though.” At Cas’s uncomprehending look, Dean rolls his eyes. “When you get to the 1% of the 1%, there’s not a lot of options to choose from.” He smirks. “FDR did it, after all.”

Cas sits down on Dean’s bed and releases the puppy to putter around on top of the covers, sniffing every crease in the duvet. “Hardly. They were fifth cousins once-removed.”

Dean shakes his head. “Figures you’d know that.”

“It’s common knowledge, Dean,” Cas protests.

“What you think is common knowledge would rock Trebek’s world.”

Cas smiles, a subtle lift of the corners of his mouth that sends Dean’s heart soaring. 

Dean ducks his head, deliberately not looking up as Cas wiggles his fingers in the air, trying to tempt the puppy into jumping for them. Cas yanks his hand back as his fingers get nipped.

Dean laughs. “What were you expecting?”

“For his teeth not to be that sharp?” Cas grumbles as he uses his other hand to pet the puppy’s head.

“Puppy teeth are crazy sharp.” Dean inspects his bag, double-checking he has everything he needs. “Have you ever had any pets before?”

“No.” Cas focuses on scratching the dog behind the ears. “My parents considered them a nuisance and a distraction.” 

Dean pats him once on the shoulder in solidarity. “I never had any growing up either. Sammy would’ve killed for a dog, though.”

Cas moves on to attending to a spot under the dog’s chin. “Inias expressed interests in cats once. Hester hates all animals; Rachel doesn’t care for them, and Hannah later got very attached to her roommate’s dog.” He pauses. “I think Gabriel had a bird in college - or he stole a pet bird. He wasn’t clear on the details.”

Dean’s eyebrows rise with each consecutive name. “Jesus Christ, how many of you are there?”

“I’m only one of five,” Cas says. “Gabriel is actually adopted.”

Dean laughs. “Black sheep of the family?”

Cas reaches for a discarded toy on the floor by his foot and waves it around. “Oh yes. Though as much as he stands out among us, he was worse with his birth family.”

“He knew them?”

Cas looks up at him. “We all know them. They’re my first cousins.”

“Why’d he leave?”

Cas sighs heavily. “His three brothers… well, Michael is the Deputy Director of the FBI, and Raphael is the Director of Quantico.”

“I can see how a sous chef didn’t fit in.” Dean cocks his head. “What about the third? Is he the Secretary of Defense or something?”

“No,” Cas says shortly. He looks up at Dean. “Lucifer left the family to start a nation-wide criminal organization.”

Taken aback, Dean eventually asks, “Is his name really Lucifer?”

Cas shakes his head. “No, but that’s what Gabriel calls him, and it caught on. His real name is Nicholas.” He swallows and yanks on the toy in the dog’s mouth. The dog growls, bending down into a lopsided crouch. 

Cas continues in an undertone, “He adopted the last name Lightman at some point; we’re not sure on the exact timeline.”

Dean gapes - _Nicholas Lightman?_ There can’t possibly be two fuckers running around with that name.

“Hold on,” Dean says, the gears of his brain creaking to fit all the pieces of the puzzle. He gapes at Cas, now petting the dog's head. “You’re saying you’re actually _related_ to the Lightbringer?”

“How do you think he has evaded the law for so long?” Cas asks rhetorically. “His father was the past Director of the FBI. His oldest brother will be the next Director, and his other brother trains all the agents he could possibly encounter.”

Dean sits down on the bed next to Cas. After a beat he says in an undertone, “You have a fucked up family. And that’s coming from me.”

Cas shakes his head ruefully. “If you can believe it, I have heard that before.”

* * *

Michael is a little nervous to present his gift to Crowley, but his fears disappear as Crowley cancels their dinner reservations in favor of delivery and names the dog Growley. Crowley takes a full hour to inspect everything about his newest pet - paws to balls. 

Michael entertains Growley while Crowley makes emergency calls to his dog trainer, his dog walker, and, weirdly enough, his insurance agent.

Apparently Milton wasn’t kidding about the price tag on these fuckers.

Michael is in the middle of a tug-of-war contest when his phone pings with a new text.

 _Cas 8:01_ _  
_ _How was the dog received?_

 _Dean 8:02_ _  
_ _Crowley loves him. Named him Growley_

Dean gives the knotted rope a few half-hearted tugs as he watches the three dots dance across his messenger screen, disappearing a few times before reappearing.

 _Cas 8:04_ _  
_ _That is a stupid name._

 _Dean 8:04_ _  
_ _That’s what I thought!_

 _Cas 8:04_ _  
_ _How is he settling in?_

Michael quickly pockets his phone, ears attuned to the call wrapping up in the next room. Crowley reappears a moment later, his dark gaze riveted by the scene on the floor of the living room: Michael on all fours on the floor, level with Growley, and engaged in a fierce game of tug-of-war.

“You’re good with him,” Crowley says, his expression soft.

Michael gives the rope a little slack, and Growley nearly trips over his own paws in his enthusiasm to gain ground. Michael sits back on his heels, smiling at Crowley over his shoulder. “He’s a good dog.”

“That he is,” Crowley says as he crouches next to Michael and Growley.

“I brought all his things with me,” Michael says as he lets go of the toy and turns to Crowley. “His crate and a few puppy pads are in my car.”

Growley whines at the lack of attention

“We can get them later,” Crowley says dismissively as he reaches over to pat Growley on the head. “My obedience trainer will be over in the morning. I will be working from home tomorrow.”

“He is a little young to be alone,” Michael sighs. He picks up the rope again, dangling it above Growley’s head so he has to jump to get it. “I’m going to miss him.”

“Miss him?” Crowley repeats, shocked. “Where the hell are you going?”

Michael lays a hand on Crowley’s knee, squeezing it gently, before meeting his eyes. “Nowhere,” he says, his voice husky. He coughs, turning back to Growley. “But this little man’s been living with me all weekend. I’ve gotten used to him.”

Crowley swallows. He says his voice gruff, “You don’t have to leave him.”

Michael starts. “I don’t?” he asks hesitantly. 

Crowley shakes his head. “You could move in. Live here.”

A slow grin spreads across Michael’s face. “Really?”

Crowley clears his throat. “You did mention you had to relocate recently. Wherever it is, I’m sure my house is nicer. And Growley is here.”

“Right, Growley,” Michael says, eyes dancing. “The real reason I would live here.”

Crowley doesn’t meet his gaze, but a slow flush creeps up his cheeks as the silence draws out.

Michael leans in for a kiss, murmuring, “I’d love to move in.”

* * *

Dean can only respond to Cas’s text after Crowley’s fallen asleep for the night. Silently, he sneaks out of Crowley’s bedroom and into the adjoining bathroom. He winces at the sight of his reflection, beard burn all up and down his neck and hickeys over his chest.

With a sigh, he turns away from the mirror and dials Cas’s number.

“Hello? Dean?”

“Hey, Cas,” Dean says, and fuck him, but half the tension bleeds from his shoulders at the sound of Cas’s voice.

“How are you?”

“Been better,” Dean says ruefully. He continues in a quieter voice, “but at least the plan worked better than I thought it would.”

“You already said he likes the dog,” Cas says, a little testily. “You _didn’t_ say if-”

Dean smiles despite himself. “He invited me to move in.”

Silence.

“Cas?” Dean tries. “Did you fall asleep on me, man? I know it’s late, but you don’t sleep.”

On the other end of the line, Cas clears his throat. “No, I’m here. I’m just… processing.”

“What’s there to process? This is a good thing,” Dean says even though it absolutely isn’t. “We’re making progress.”

“Right,” Cas says, his voice a tad hollow, “progress.”

Dean waits for Cas to elaborate, but when nothing comes, he says, “Anyway, wanted to update you on the situation.”

“I appreciate it.”

Dean bites his lip, the fingers of the hand not holding his phone gripping the marble sink countertop with unnecessary force. Fuck, Cas sounds mad.

“I figure I’ll move out over the next couple of days. I don’t want to rush Crowley, and I think he’ll be picky where I put my stuff.”

“I’ll start packing your things tonight.”

“What? Cas, you don’t have to do that.”

Cas sighs. “I might as well.”

“It’s late,” Dean protests lamely. “You should go to sleep, man. We’ll figure it out in the morning.”

“I probably won’t get to sleep for a few more hours. I might as well be productive.”

Dean swallows, an irrational bitterness rising in his throat. A part of him, a stupidly large part, wants his shit to stay with Cas, like even if Dean can’t be there, at least a part of him can be - can remind Cas of him. But no, Cas wants Dean gone from his space as soon as possible.

“Right, okay,” Dean says, defeated. “I’ll pick everything up after work tomorrow?”

“Unless you’d prefer movers to transfer your things.”

“I don’t have that much.”

“Ah, right,” Cas says, awkward.

“Right,” Dean echoes. “Night.”

“Goodnight, Dean.”

Dean buries his head in his hands, his vision going blissfully dark. He breathes in deep, the scent of exquisitely expensive potpourri and bath soaps filling his nostrils. 

His heart aches as he sits down heavily on the lid of Crowley’s toilet. The porcelain isn’t even cold against his ass - the benefits of never having to worry about running the heating bill too high to pay for food. 

He stares out at Crowley’s pristine bathroom, not seeing any of it.

* * *

Cas didn’t touch Dean’s underwear drawer. 

Dean stares down at his intact mismash of boxers (and various other underthings) and releases a little sigh of relief that Cas didn’t go snooping after all. 

“Hey, Cas,” he calls, listening for Cas’s footsteps outside his bedroom. “Looks like you forgot to pack some of my shit up.”

In the doorway, Cas pauses, reddening. “I did not _forget_ ,” he huffs, shuffling in place like a discontented bird. “If you - I mean, I did not want…” He shifts his weight to his other foot.

Dean laughs. “Scared of my cooties, man?”

Cas scowls. “Maybe I wanted to spare you my cooties instead.”

“Uh huh,” Dean hums, a wide grin splitting his face. “Big G-Man is afraid of a few pairs of boxers.” He tips his head in Cas’s direction. “I gotta say, I’m glad my personal safety is in your hands.”

Cas’s frown deepens as he glares at the offending drawer. “I did not feel it was appropriate.”

Dean grabs a fistful of his underwear, careful to keep the brighter pairs in the middle of the pile and out of sight. He says in an almost casual voice, “I mean, you did have your tongue in my mouth at one point. Not like we have many boundaries left.”

Cas averts his gaze. “I think we have a fair few,” he says evenly.

Dean tosses him an easy smile over his shoulder as he shoves his bounty down deep into his duffel bag. How cool is it they can joke about the time they made out? The time Dean told Cas he was the best thing in his life? The time when Dean was half in love with him? 

At least, Dean can joke. Cas can listen, since he’s still trying to get a handle on the whole humor thing. Baby steps. 

Dean pulls the handle of the drawer in the nightstand and reaches in to stash his dildo in his bag too.

Behind him, Cas chokes on air.

Dean whirls around, refusing to be shamed. “You got something in your throat, Cas?”

Cas, already pink in the face, flushes a deeper shade of red. “No.”

Dean huffs an exasperated sigh. “It’s a perfectly normal thing to have,” he says brusquely as he zips his bag shut.

“I know that. But...”

“But what?” Dean prompts.

Cas shakes his head. 

“Fine, keep your dirty thoughts to yourself,” Dean says. He strides past Cas, patting him once on the shoulder. “Just remember, dude, sharing is caring.” He winks.

Cas freezes in place, mouth falling open. “I didn’t think…” he says faintly.

Dean waits impatiently for Cas to finish, hands clenching on the straps of his bag. With a forced smile, he says, “Something to think about while I’m gone, maybe.”

“I should think about dildos in your absence?” Cas asks, completely bewildered.

Dean stifles a laugh. “No, not dildos.” He hikes his bag further up his shoulder. “It’s … you never had anyone over.”

“You were here,” Cas points out.

“You still could have had company.” At Cas’s confused squint, Dean sighs and shakes his head. “If I cramped your style, dude, I didn’t mean to.”

“I don’t really have a style to cramp, Dean.”

Dean’s brow furrows. “Seriously?”

Cas lifts his hands in the air in a helpless gesture. “You’ve seen how I live, the kind of person I am. You’re honestly surprised I can’t tempt someone into my bed every night?”

“Not every night…” Dean drifts off, “but yeah.”

Cas's mouth twists. “I told you, I haven’t had sex in years.”

Dean’s eyes nearly bug out of his head. “That was true?”

“I also told you,” Cas continues irritably, “I didn’t lie if I could help it.” 

“But still,” Dean says helplessly, “I thought _that_ at least was a ploy to keep me on the hook.”

“By not sleeping with you?” Cas asks, head tilting quizzically. “Wouldn’t that have had the opposite effect?”

Dean’s foot scuffs against the carpet. “It keeps a mark interested,” he mutters, “playing hard to get. Makes ‘em want it more.”

Cas’s face falls. “Oh.”

“Yeah, well,” Dean says as he hitches an unconvincing smile onto his face. “I dunno why they pay you to look at spreadsheets all day. You could catch bad guys like me easy as pie instead.”

Cas’s expression softens. “You’re not a bad man, Dean.”

“Try telling that to all my victims,” Dean says brusquely as he pushes past Cas out into the living room.

“Dean.”

Dean doesn’t pause in his march towards the front door. He drops his duffel on top of the suitcase Cas already packed for him.

Cas doggedly trails behind. “I don’t think-”

“Drop it, Cas,” Dean says shortly.

“No,” Cas says, the stubborn son of a bitch, “You need to hear this.”

Dean whirls around to say in a hard voice, “I need to hear what? That I’m secretly a good person because I didn’t really want to do what I did?” He sucks in a breath before adding, “You ever heard, ‘it’s not what I say, it’s what I do that defines me’?”

Cas opens his mouth, eyes narrowing into a squint. “Did you just quote Batman?”

“Not the point, Cas,” Dean shakes his head, “I can talk about my _feelings_ about what I do ‘till I’m blue in the face. It doesn’t get their money back. It doesn’t make right whatever shit I fucked up in their heads by leaving.”

Cas opens his mouth, but no words come out.

“Yeah, that’s what I thought,” Dean says, face pinched. “I’m gonna go.” He bends down to shoulder his backpack and grab his duffel. In his other hand, he grips his suitcase handle.

Cas looks at him, his expression almost sympathetic, and Dean has to look away before it turns to pitying. Cas murmurs, almost too quietly for Dean to catch, “You can call me, you know.”

“Every Tuesday and Thursday at noon sharp, I remember,” Dean says bitterly. “I can keep a schedule.”

Cas shakes his head. “No, not for debrief.”

“Why? You need more help feeding yourself?”

Cas snaps his mouth shut. Lips pressed together, he edges past Dean to open the door for him. “Never mind.”

Dean doesn’t move. Begrudgingly, he adds, “’Cause you can always look online for recipes. You got down the techniques so you don’t set appliances on fire again.”

Cas sighs. “Yes, I know, thank you.”

Dean turns to face him fully. “You don’t need cooking help, do you?”

“No.”

“What is it, then?”

Cas briefly closes his eyes. “I was going to ask you to call if you needed a friendly ear,” he says, a strangely defeated tone to his voice. He adds, his cheeks pink, “but not if you think it will be a distraction.”

Dean’s brain sluggishly absorbs the full meaning of Cas’s words. “You want me to call...” he searches for the right words, feeling a little stupid for needing Cas to spell it out for him, “if I feel like it? To do what, shoot the shit?”

Cas stares hard at the span of wall over Dean’s left shoulder. “That was the general idea,” he says stiffly.

“Okay.”

Cas’s eyes whip back to Dean’s. “Okay?” he asks.

Dean straightens. “Yeah, I can do that.”

Cas smiles.

**Notes for the Chapter:**

> Next chapter up Monday!


	7. The Breakdown

**Summary for the Chapter:**

> “I’ve never lived in one place for more than a year,” Michael says, turning to smile down at Crowley, whose brows start to smooth as he catches on. “When I arrived in LA, I never expected to fall for anyone,” Dean swallows, the truth stinging on his tongue, “I wasn’t looking for love or even a partner. But I found both anyway, over morning coffees and late nights while he worked overtime and I pretended to.”
> 
> There are more laughs.
> 
> Michael gets down on one knee.

Michael settles in Crowley’s life like a missing puzzle piece. He gets up early to make Crowley breakfast and his morning cappuccino before Marco drives both of them to work. Michael stops by Crowley’s office to sneak quick kisses - but not quickies, as Michael points out Crowley has an image to maintain. After they get driven home, they walk their dogs. Dean makes dinner Sundays and Wednesdays; on Friday they go to Ninth Circle; and on Saturday they go on a date.

At midnight a couple times a week, Dean sneaks out and calls Cas, who is usually awake because he’s secretly a vampire. 

They don’t talk about Crowley. Dean asks for updates on Sam, Charlie, and Jo. He tells Cas about the new trick Growley learned in obedience school. Cas waxes poetic about the brisket Gabriel added as a weekend special to his menu. Dean doesn’t think the pear and apricot marinade sounds right, but maybe that’s because the best brisket he ever had was at Oma Bass’s seder. He argues about it with Cas for a full half-hour.

Tuesdays and Thursdays, when Crowley has his biweekly meetings with other senior partners, Dean conference calls with Milton, Balthazar, Cas, and, rarely, Uriel.

The Feds keep bugging him to speed up the proposal. Dean wracks his brains for the perfect opportunity.

Dean can’t whisk Crowley away to a romantic location - Crowley’s vanity means he would want everyone back home to know and witness the big moment.

Dean can’t ask in Crowley’s favorite restaurant - Crowley would find the scenario horribly pedestrian.

He has to make it public, unique, special. No big deal. It’s just Dean’s life on the line.

The idea comes to him as he books their plane tickets and hotel room for Daimonion’s annual company conference in Seattle. Dean scans the schedule in his inbox to confirm the dates.

It takes place in three weeks, and on the last night, there will be a black-tie party at the top of the Space Needle. Crowley was invited, of course, along with all the top dogs at Daimonion. Everyone who’s anyone at the company will be there.

Bingo.

The night the Feds have been waiting for arrives after a whirlwind week of boring-ass meetings and seminars. Halfway through the party at the top of the Space Needle, Michael pushes open the door to the restroom - thankfully empty. He takes a moment to try to relax and breathe. The little box in his pocket weighs a ton, and he’s sweating and his hands are shaking. His bowtie is slowly strangling him.

Why couldn’t they have had their conference in Juneau? For fuck’s sake, it’s the first week of September. Fall weather should be here already. It barely feels like he’s left LA summer behind.

God, if only Crowley were more like Pamela - Dean proposed to her over Chinese takeout in her own goddamn apartment, just the two of them.

No, instead Dean has to put on this whole dog and pony show. He has to pretend to care about Eve’s idiotic Harvard-bound son, Bart’s new summer home, and Ruby’s beef with a city councilor over a new playground outside her condo.

Any minute now, the meal will start and Michael will make his speech and pop the question.

Dean has proposed seven times, but the nerves never go away.

Usually his handler would give him a pep talk before the Big Moment, but the Feds have been keeping Charlie busy in North Dakota, faking business as normal for the Lightbringer and working with Sam to unearth more evidence for their case.

Dean’s finger hovers over Cas’s name on his phone screen for too long before he presses it in a moment of weakness.

“Dean?” Cas picks up halfway through the first ring. “Is everything okay? Did it happen?”

Dean exhales sharply. “Soon.”

“Ah,” Cas falters. “So not yet.”

This was such a stupid idea. He squeezes his eyes shut as he says, “Never mind, I’ll check in later when it’s all over. I shouldn’t have called now.”

“Wait,” Cas says quickly, “I was just surprised.”

Dean smiles wryly at his own reflection, in a perfect tuxedo (Crowley’s tailor can really work miracles) with gelled-down hair. “You didn’t think I’m the type to get cold feet?”

“Is that what this is?” Cas asks. A door closes in the background, and some ambient noise from Cas’s end cuts off.

“Yeah.”

“Why?”

“Why would I get cold feet before asking someone to marry me?” Dean asks incredulously.

“Yes,” Cas says, a tad impatient.

“I don’t know,” Dean says sarcastically, “What if he says no?”

“Why would he say no?” Cas asks, and Dean would give anything to see Cas’s face right now. He doesn’t sound like he is making fun of him. He sounds genuinely confused as to why anyone would deny Dean their hand in marriage.

Dean releases a weighty sigh. “Maybe he thinks I’m a gold digger.”

“We’re monitoring his house, emails, and phone calls,” Cas points out, “so we know that’s not true. He’s not going to say no.”

“How can you be so sure?” Dean asks, his voice small. 

He regrets the question before the words are out of his mouth, but he can’t take them back before Cas responds, “Because I know you.”

“Then you know all the reasons to say no.”

Cas doesn’t jump to reply on the other end of the line, and Dean can almost see him chewing on his lip, sitting in his office chair, behind a desk adorned with a bee-themed calendar and a picture of Gabriel in front of his first restaurant. “You said the cons only work because you show them a part of your true self," Cas says, "Have you ever considered perhaps all your marks committed to you _because_ of that true part of yourself you show them?” 

“They fall for the lies I feed them, Cas,” Dean says bitterly. “They don’t fall for me.”

“You can’t have it both ways,” Cas says, almost annoyed. “Either, your true self draws them in and that’s the key to your success, or it’s a wasted effort on your part since they only love the part you play.”

Dean’s jaw clenches. “Look-”

Cas continues in a low voice, almost to himself, “So many people have fallen in love with you, and I truly do not understand how you think you deserve none of it.”

Dean shakes his head. “I don’t.”

Cas doesn’t have an immediate comeback. Eventually, he says, “You deserve a great deal more than you give yourself credit for.”

Dean doesn’t bother to hide his scoff of disagreement.

“But I suppose that’s a discussion for another time.” Cas sighs. “I realize you’re really nervous, but I don’t think it really matters what you say tonight. As long as you don’t embarrass him or insult him, he’s agreeing to marry you based on the past months you spent together - not one speech.”

“Yeah,” Deans says as he runs a clammy hand down his face.

“If I were in Crowley’s shoes, I wouldn’t say no,” Cas adds. And doesn’t _that_ send Dean’s imagination into overdrive.

Dean swallows. “Good to know,” he says weakly.

“I have faith in you, Dean.”

When Michael stands during dinner roughly thirty minutes later, his hands are still shaking, and his body is still too hot. He fumbles in his pocket for the notecards with his speech but lets them flutter to the table as he meets Crowley’s confused expression on his left hand side.

“Ladies and gentlemen,” Michael starts with a conciliatory dip of his head, “Thank you for allowing me to hold the floor. I’ll do my best to be brief. As many of you know - especially Guthrie, I can’t thank you and HR enough - Mr. MacLeod and I are dating. I’m sure you’ve seen pictures of our new puppy, undoubtedly showing a soft side many of you didn’t know Mr. MacLeod had.” 

There are a few laughs. 

“I’ve never lived in one place for more than a year,” Michael says, turning to smile down at Crowley, whose brows start to smooth as he catches on. “When I arrived in LA, I never expected to fall for anyone,” Dean swallows, the truth stinging on his tongue, “I wasn’t looking for love or even a partner. But I found both anyway, over morning coffees and late nights while he worked overtime and I pretended to.”

There are more laughs.

Michael gets down on one knee. He meets Crowley's gaze squarely. “During my job interview, you made me promise in writing I would stay with you for three years. Now, I know it wouldn’t be legally binding, but I’d like to verbally amend our agreement,” Over the latest round of laughter, he reaches into his pocket and pulls out the ring box, “to forever. Sir, will you do me the great honor of marrying me?”

A waiting photographer snaps a picture.

Crowley blinks, coming back to himself. He reaches for Michael’s hand, squeezing gently. “Yes,” he says hoarsely, “I’ll marry you.”

Michael’s smile is blinding as he leans in for a kiss, and they break apart as the clapping starts. He gets to his feet, still smiling, “Thank you, everyone, for your time.”

“Champagne!” Crowley says loudly. He basks in the applause of the assembled executives, “I got bloody engaged!”

“I’ve already ordered it,” Michael says in an undertone, tipping his head towards the incoming half-dozen waiters all carrying champagne bottles.

Crowley presses a smacking kiss to Michael’s cheek. “You do think of everything, don’t you?”

Michael ducks his head. “I was just being hopeful, sir.”

* * *

After they return to LA, Dean nearly chokes on a piece of his coq-au-vin as Crowley brings up wedding plans over dinner the very next Monday.

“We will need to book a venue, of course,” Crowley is saying as Dean tries to get his face back to its normal color. “I’m thinking a Spring ceremony.”

Michael bites his lip. “Isn’t that a bit far out?”

Crowley waves a hand. “It takes time to prepare for a wedding, Michael. If you think about it, it’s actually short notice. We’ll barely have time to send out Save the Dates. Next weekend we’ll tour venues, of course. There are a couple of places large enough for all our guests, but no doubt they’ll get booked up quickly.”

Michael keeps his eyes trained on shredding a piece of perfectly cooked chicken with his fork. “Is that what you did for your last wedding?”

Across the table, Crowley pauses, a speared potato halfway to his mouth. “Perhaps,” he says as he reaches for his scotch instead. “Don’t really remember, to be honest.” He takes a large gulp. “Too much champagne, you know.”

Michael nods along. “Did you enjoy it?”

Crowley hides his scowl behind another sip of his drink. “My 500-person spectacle that cost more than the GDP of several island nations? Not especially.”

Michael lets the silence sit between them as Crowley recalls his first wedding.

“Do you really want to do that again?” Michael asks as he leans over to refill Crowley’s glass without prompting.

Crowley doesn’t answer at once. He viciously spears another potato and washes it down with more whisky.

“Because I don’t,” Michael continues, “I don’t have any close family left, and I’ve only made a few friends here. A large ceremony is… intimidating, to say the least.”

Crowley sighs. “Leaving off all my influential business associates will not go over well.”

“Maybe there’s a compromise?”

Crowley lowers his fork thoughtfully. “What are you thinking?”

“A small ceremony and a large reception a few weeks later?” Michael tries, “Or we could have a real one-year anniversary party. Nobody does those these days.”

Crowley mulls the suggestion over, swirling the last drops of scotch in his glass. “That is true.”

“If we keep it small,” Michael ventures, “we can get married so much sooner.” He reaches over to cover Crowley’s hand with his own. “And I don’t want to spend any more time not legally bound to you.”

Crowley’s eyes gleam. “What were you thinking, then?”

“Three months?” Michael asks hopefully.

“You’re insane,” Crowley says, no hint of an insult in his voice. “But if anyone can pull off a wedding in three months, it’s you.”

Michael ducks his head. “I can try.”

* * *

Later that night, Dean waits anxiously as the phone rings, watching as Growley circles the same palm tree for the third time.

“Hello, Dean.”

“Hey, Cas,” he says, already breathing easier. “What’s up?”

A few computer keys clack on the other end of the line. “I’m wrapping up work, actually.”

“Dude,” Dean says as he switches hands to read the face of the fancy watch Crowley gave him all those months ago. “It’s almost midnight.”

“Someone had to make serious inroads in the case this evening,” Cas says mildly, “which means paperwork. Who do you think is managing the budget for your upcoming nuptials, anyway?”

“Crowley,” Dean says promptly.

“I don’t think Crowley is going to pay for your hidden wire,” Cas says, and Dean can almost hear the smile in his voice, “or overtime hours for half a dozen undercover agents for a whole weekend.”

“Sorry for all the extra crap.”

“Don’t be,” Cas says. “I’m making sure you’re adequately protected during a dangerous sting operation. In fact, I’d worry if it was anyone else doing this work.”

Warmth blooms searing and bright in Dean’s chest. He lets Growley lead him towards the other side of the street, listening with half an ear as Cas keeps typing in his ear. It’s an unbearably soothing noise after spending so many days falling asleep to it outside his bedroom door.

“Hey, I got an important question for you,” Dean says.

“Yes?”

“Wanna be my best man?”

The typing stops. “Excuse me?”

Dean unwinds part of the leash from around his hand. “I mean,” he says as the doubt creeps in, but he soldiers on, “normally Jo would step in, you know, someone who I trusted implicitly to have my back. But she’s not here.”

Silence on the other end.

“Would you like her to be?” Cas asks eventually. “She and her mother are currently at a safehouse and doing remote work with Ms. Bradbury, but we could get her to California relatively inexpensively.”

Dean snorts. “She’s already burned. She was Crowley’s dog walker, remember? The one who probably took off with a boatload of his money?”

“Right,” Cas says, and Dean can almost hear the embarrassment in his voice that he forgot.

“Anyway, it was just a thought,” Dean says. He tugs Growley along. “If you don’t want to, it’s fine. I already talked him into a small ceremony, so we might not have best men at all.”

“Do you think I could do it?”

“What?” Dean cracks up at the uncertainty in Cas’s voice. “Of course you could pull off pretending to be my friend.”

Cas sucks in a quick breath. “Dean, you know-”

“Chill out. I’m just messing with you. Water under the bridge.”

“I - well then,” Cas fumbles, “It would be my honor to be your best man.”

“Awesome,” Dean says, fist-pumping the air. “I’ll make up some bullshit about knowing you from my last job. I’ll forward you my resume.”

“Yes, please do,” Cas says distractedly.

Dean urges Growley on from sniffing around a tree he clearly has no intent on peeing on as he tells Cas, “Guess you’d better get going on planning my bachelor party, best man.”

“I am not spending government money on hookers and blow,” Cas deadpans.

Growley jumps at Dean’s shout of laughter. “Who the hell taught you that?”

“Taught me what?”

Dean chuckles. “I don’t think hookers and blow came up in Finding Nemo.”

“My brother. Gabriel settled on a ‘strip club crawl’ for his bachelor party.”

“Sounds like a fun time.”

“It was not.” Cas adds sourly, “Magic Mike did not prepare me for the experience.”

Dean grins. “They’re not so bad. I worked at a strip club for a job once. Backstage, there’s a whole other vibe. Never met a closer group of people. They took a while to warm up to me, but, lemme tell you, once they did, it was a whole other ballgame. I got the mark in record time with their help.” He pauses. Cas had been suspiciously silent on the other end of the line. “Did I lose you?”

Cas clears his throat. “You worked at one of those establishments?”

“Yeah,” Dean says slowly.

“...The ones with the poles?”

“They all have poles, dude.”

“So you… danced?”

Dean smirks. “You want a demonstration?”

“Um, not right now.”

* * *

Crowley and Michael find their wedding venue two weeks later, after inquiring with eight other places.

Thank god all eight proprietors were more intimidated by Cas's badge than Crowley’s bank account. Not for a lack of trying on Crowley’s part - he promised to pay his favorite five-star hotel 150% over asking price if they bumped the Trans’ 40th anniversary party. The hotel declined after a stern visit from Agent Cas “Badass” Novak.

But the loss of the hotel is the last thing on Crowley's mind as he watches Michael fall in love with St. Mary's Convent. The nuns had moved on after a freak gas explosion in the 70s, but the side church was left intact.

(St. Mary’s Convent is also a snappy fifteen minute drive from the FBI and has a secure perimeter. Someone was looking to keep those nuns fenced in good.)

As they wrap up their visit, Michael tells Crowley his mother’s name was Mary, and the church looks nearly identical to the one he occasionally visited as a young child. He stares around the sanctuary, his eyes misting over. “If my mother can’t be here in person for my big day, maybe she’s here in spirit.”

Crowley nods along, fingers tapping against his leg. “Of course, darling,” he says, distracted. They have a budget meeting back at the office at four PM.

With a benevolent smile, the priest says, “We can accommodate any of your wishes here at St. Mary’s.”

“Great,” Crowley says. “My people will be in touch with your people about the second week of November.”

The priest’s eyes widen in alarm. “Oh no,” he mutters.

“No?” Crowley repeats, a clear warning in his tone.

The priest looks down. “We will actually be hosting a group of Italian nuns for the entirety of November.”

“So?” Crowley barks.

The priest shrugs helplessly. “I’m afraid we won’t have room.”

“Can’t you reschedule?”

The priest sighs. “The Holy Sisters of Malta’s funds are already stretched thin after an ancient relic of theirs was stolen. There is no way they can change their plans.”

“Then move them somewhere else for the weekend!” Crowley blusters.

The priest shakes his head. “It cannot be done.”

“If it’s about money-”

“It’s not about money,” the priest says over Crowley’s protests. “I don’t wish to go into the politics, but upsetting them would be catastrophic for St. Mary’s.”

Michael jumps in, “What do you propose we do, then? We _have_ to get married here, Father!”

The priest dips his head. “Of course, and we thank you for your dedication to our humble church. May I suggest an alternate date?”

“We’re not getting married in the middle of the bloody winter.”

Michael pats his knee reassuringly. “Are there any October dates available?”

Crowley tenses under Michael’s hand. “Impossible,” he mutters under his breath.

“Perhaps the weekend before Halloween?” the priest offers.

“Impossible,” Crowley echoes, slightly louder. “We can’t plan a wedding in six weeks!”

Michael quiets him with a look. “I can,” he says, his tone brooking no argument.

Crowley’s eyes go round. He can count the number of times Michael has stood up to him on one hand with fingers to spare.

“I will never work harder on anything, I promise you,” Michael continues, his face almost unbearably earnest. "If it’s a choice between next month or December, I know what I would prefer."

Crowley’s expression loses some of its hard edges. “You’d better not slack off at the office,” he says gruffly.

“Of course not,” Michael says, affronted by the very idea.

“We’ll have to get the best wedding planner in the city.”

“I will give them a call in an hour.”

Crowley nods. “Right, well,” he says coolly as he turns to leave, “Now we’ve gotten that all straightened out. We’ll be going. My people, your people, yadda yadda.”

Michael grabs his hand. “Can you give me a minute?” he asks. “I’d like some time alone in the sanctuary.”

“Oh, why not,” Crowley says sarcastically, “We’ve already blown past our four PM. I’ll be in the car.”

Michael leans in for a quick kiss. “Thank you, sir.”

Both Michael and the priest watch Crowley stalk down the aisle and out the doors.

“What a bloody nightmare,” Balthazar breaks the silence.

Dean rolls his eyes. “He doesn’t do well when he’s rushed.”

Balthazar shrugs out of his robes with a grimace. “Too bloody hot,” he says by way of explanation as he drapes them over a nearby pew. “So,” he turns back to Dean, “That wasn’t so hard, was it?”

They both turn at the sound of footsteps from the direction of the rectory. “It doesn’t matter if it was hard,” Milton says, Cas hot on her heels. “He agreed to the date.”

Dean crosses his arms across his chest, stares them all down. “You didn’t think I could do it.”

Milton looks away. “We try to plan for all contingencies,” she says delicately.

Balthazar’s expression turns sardonic. “Would you like a gold star?”

Cas tries to hide his smile. He doesn’t succeed.

* * *

 _Dean 5:03_ _  
__Who’s setting up the wedding planner bit?_

 _Cas 5:10_ _  
__Anna, Bal, and I are talking to Uriel about it this evening. When we have their identity established, I’ll email you their contact information, website, and schedule to coordinate an in-person meeting._

 _Dean 5:11_ _  
__Probably will to be next Mon morning_

 _Cas 5:16_ _  
__We can work with that._ _  
__Are there any specifics this person should have to convince Crowley of their authenticity?_

 _Dean 5:16_ _  
__A hefty deposit fee and airtight contract_ _  
__He’ll want the best aka the most expensive_ _  
__He’s also got a 6th sense for being cheated on a contract deal_

 _Cas 5:19_ _  
__That’s ironic._

 _Dean 5:20_ _  
__You’re telling me_

In the middle of his late-night walk with Growley, his phone pings with a new text from Cas. He opens the link to Elysium Weddings and Events Cas with some trepidation.

The page loads, and he can see Charlie’s hand all over it. The header banner shows a goddamn Moondor tent, festooned with photoshopped flowers to look vaguely wedding-ish. The main menu is written in an elvish lookalike font. No doubt the page is bugged to the gills with malware, so Dean carefully inspects without tapping on anything.

He scrolls down the bogus testimonials from happy couples and the types of weddings and events Elysium specializes in with vague disinterest. At the very bottom of the page is the photo of the CEO, John P. Jones.

Dean dials Cas’s number with shaking hands.

“What the hell?” Dean demands the moment Cas picks up.

“Hello, Dean.”

“Don’t _hello, Dean_ me,” Dean hisses as he tugs Growley away from a bush before he can get to third base. “What the hell are you guys playing at?”

“I assume you’ve received my email.”

“You bet your goddamn ass I have. What happened to keeping Sam in bumfuck nowhere, South Dakota?”

Cas sighs. “We had to make a decision, and Sam was our best choice.”

“What makes you say that?” Dean asks through clenched teeth.

“The budget-”

“Screw your fucking budget!” Growley jumps, looking up at Dean with wide eyes, “It’s my brother’s ass on the line-”

“The budget is already in a position which will draw undue attention at the Bureau,” Cas says loudly over him. “We need to keep this operation small, Dean, and when it came down to either your brother or another agent, we went with the best choice.”

“Small?” Dean repeats. “You worried about leaks?”

“Every single operation looking into Lightman has failed,” Cas says seriously. “The FBI has its inefficiencies and flaws, but it is not _incompetent_.”

Dean’s shoulders slump as he bends down to pat Growley reassuringly on the head. “And you already know Sam’s clean.”

“He has so far proven his dedication to taking down Lightman,” Cas says evenly. “And his inside knowledge of how you work, how the con works, and of this case, is unparalleled.”

He fights with himself before asking, “Why didn’t you check with me, man? He’s _my brother._ ”

Cas doesn’t answer at once. “I know, Dean. But I have to prioritize the case over your feelings. We asked Sam’s permission, of course. He wasn’t conscripted into this.”

“Did you say it would help me?” Dean asks, resigned.

“Yes? Was that not the right way to approach him?”

“You can approach him any damn way you want,” Dean says, mouth twisting. “You’re the good guys, after all.”

“You’re angry.”

“What clued you in, Dr. Phil?” Dean makes a frustrated noise. “Look, I got your message. I’ll schedule a meeting with Crowley and Sam.”

“Dean-”

“Night, Cas.” 

He hangs up before Cas can get a word in.

* * *

Dean tosses and turns all night, switching unevenly between elation and panic at finally seeing Sam in person. It’s been a year and change since they’d gotten coffee in a hippie dippy cafe in Chicago to catch up. 

He watches the sun rise over the back gardens, sipping the strongest cup of black coffee he can make, before slipping inside and making Crowley his breakfast.

At work, he gets his head in the game. Michael has to run and analyze a billion reports by the end of Q3, and make appearances in preparation for his wedding. He sends Crowley the Elysium website and tells him he already booked a slot for next Monday morning, exactly one week away.

He works straight through lunch, which he usually only pretends to do. 

He doesn’t call Cas, and he doesn’t pick up when Cas calls him at their usual time.

Over the rest of the week, even Crowley notices his dedication, calling him into his office for a quick chat about the Roman account on Friday. In a rare show of empathy, he asks Michael how he is doing.

Michael spins a tale about how he sweet-talked Mr. Jones’s secretary into squeezing them in last-minute. He assures Crowley of Elysium’s exclusivity, and shares his plans to make their affair extra-appealing to Jones.

Crowley argues some of the plainer designs Michael favors, pushing for more extravagance.

“Even if the whole world won’t see,” Crowley says, “we will. Isn’t that enough?”

Micheal dips his head. “Of course, sir.”

“Good,” Crowley says as he scribbles something on a printed-out graph. “You are worth it, you know.”

“Sir?”

Crowley sighs before looking up. “You keep denying yourself things, Michael. I’ve noticed.”

Michael freezes. “I have?”

Crowley nods slowly. “I’m not telling you to go out and buy a Ferrari, but you can indulge every so often. Everything you do always connects back to me or to the company. You can do things for yourself, you know.”

Michael bites his lip. “Like what?”

“I don’t bloody know,” Crowely says mildly. “But I suggest you figure it out unless you want to go mad from all the duties you’re taking on. You’re the best PA I’ve ever had, but it’d take a miracle for you to keep going like this.”

Michael unsticks his tongue from the roof of his mouth. “Yes, sir,” he mutters before he ducks out of Crowley’s office, face burning.

“Oh, and send Mickey over when you get a chance!” Crowley calls, “I want to reject his request for _paternity leave_ in person.”

Back at his desk, Dean pulls out his phone.

 _Dean 12:47_ _  
__There’s a 24 hr diner at Gamble and 1st_ _  
__Breakfast tomorrow at 9?_

Sam texts back less than a minute later.

 _Sam 12:47_ _  
__Yes, of course! See you soon._

* * *

Dean’s tentative good mood evaporates as Cas’s Lincoln pulls up in front of the diner at 8:58.

Sam, on his long legs, easily outpaces Cas on their way towards Dean’s booth. He wraps Dean up in a hug, muffling Dean’s weak, “Hey, Sammy.”

“Hello, Dean,” Cas says when Dean and Sam break apart.

“Cas,” Dean acknowledges stiffly.

Sam looks curiously between the two of them but doesn’t comment as he slides in across the booth from Dean. Cas takes a seat opposite too, and Dean squashes down the feeling they’re ganging up on him.

“So,” Sam asks in the ensuing silence, “How’re you doing, Dean?”

“Been better,” Dean says shortly, his gaze boring into Sam’s face. “How are you doing, Sam? Here, on the West Coast, back in the game _you just left?”_

Sam exhales an explosive sigh. “That’s how you’re going to play it? We haven’t seen each other in a year, and the first thing you do is jump down my throat-”

“Hell yeah, I will,” Dean thunders back, “because I can’t believe you’d be that goddamn _stupid-_ ”

“You’re about to take down the Lightbringer. I wouldn’t miss it.”

“It’s not a rollercoaster, bitch,” Dean retorts. “You can skip this one - and you fucking should. Go back to South Dakota. I’ve got it handled.”

“Do you?” Sam asks in a horribly superior tone of voice, “Because Castiel has been telling me-”

Dean rounds on Cas. “What have you been saying behind my back?”

Cas startles like a random circus audience member picked out of the crowd to join the trapeze act. “I don’t - I haven’t - excuse me?”

“What has Cas said, huh?” Dean turns back to Sam. 

Sam narrows his eyes. “So you don’t have it handled.”

Dean grimaces; he’s too damn old to get caught in Sam’s mind games. “I do have it handled, okay?”

Sam’s retort is cut off by their waitress. “Hello,” she says brightly, her smile faltering as she takes in the tension around the table. “What can I get you?”

Once she disappears, they sit in awkward silence until she comes back with coffee for Cas and Sam.

Cas breaks first. “How have you been, Dean?”

“Peachy,” Dean says with a sickly sweet smile. “Just peachy, Cas.”

Like a bird shot out of the sky, Cas’s face falls, and Sam’s eyebrows fly to his hairline.

Dean refuses to feel guilt. He sips at his coffee.

Sam shoots them curious looks. When neither Dean nor Cas open up from sheer psychic force alone, Sam points out, “You’re the one who invited me here, Dean. If you’re gonna be all,” he waves a large hand in Dean’s direction to encompass his _Dean-ness,_ “There’s no point in staying.”

Dean has a nearly visceral reaction to Sam walking out on him again. “No,” he says hoarsely, “Stay.” He runs a hand through his hair, trying to get his bearings. “I’ll play nice.” He rolls his eyes. “How’re you settling in LA? Where are you living, anyway?”

“With Castiel,” Sam says, surprised Dean had to ask.

Dean blinks, his gaze sliding over to Cas before he can stop himself. Apparently Cas can swap one Winchester out for the other as easy as pie. He snaps his attention back to his brother. 

“And that’s going OK?” 

Next to Sam, Cas bristles. 

Dean ignores him.

“Sure,” Sam says, once again looking from Dean to Cas and back again before responding. “Much better than rooming with Charlie, at any rate. Did you know she talks to herself?”

Dean grins. “When she gets into the zone the Incredible Hulk could bash through the wall behind her, and she wouldn’t notice. How’s she doing? And Jo?”

Sam is midway through retelling Jo’s fight with their FBI handler over her knife collection when their food arrives.

Cas uses the break in storytelling to tell Dean, “You missed your last check-in.”

Dean freezes, a piece of bacon halfway to his mouth. “Come on,” he complains, “No shop talk over breakfast. It’s bad enough you tagged along to breakfast with my brother.”

Cas wilts.

“Dude,” Sam hisses. “What the fuck is your problem?”

Dean shakes his head. “Stay out of it, Sam.”

“Hard to when I’m _sitting right here.”_

Cas sighs. “It is not of import,” he waves off Sam’s concern. “Dean is angry at me for bringing you into this.”

“But I chose this,” Sam says mutinously.

Dean points an accusatory strip of bacon at Sam’s face. “You also chose Jar Jar sheets for your birthday. Sometimes you choose stupid things, and it is my role, as your big brother, to tell you you’re being a dumbass.”

“I was seven.”

“So you have a long history of making stupid decisions,” Dean says flatly. “Not exactly disproving my point, Sammy.”

Sam’s jaw clenches. “You can’t pull the big brother card here.”

“Watch me.”

“I’m a fucking adult,” Sam fumes. “And _I’m_ the one who got the Feds involved in the first place, so when they asked if I was going to help end it, I wasn’t going to say no.”

“Why the fuck not?”

Sam sets down his knife and fork. “Because if it all goes to hell, it’ll be my fault. And I can’t live with knowing I didn’t go all in when you needed me.”

Dean’s anger ebbs with each additional word out of Sam’s mouth. “None of this is your fault,” he says eventually.

Sam scoffs and eats more of his fruit salad.

“I mean it,” Dean says, his voice uncharacteristically serious.

“Dean is right,” Cas offers. “Technically, Lightman is to blame for all of this.”

Dean sighs. He’d almost, impossibly, forgotten Cas was there. “Sure, let’s blame him,” he mutters.

Cas’s eyes narrow. “That means this isn’t your fault either.”

Dean shovels more waffle in his mouth.

* * *

“Can you give me a minute with my brother?” Dean asks Cas after they’ve paid the bill.

Cas hesitates.

Dean rolls his eyes. “What now?”

Cas fidgets with his napkin. “I’m not supposed to leave Sam unattended.”

“I’m twenty-eight, dude,” Sam gives Cas a funny look, “not five. I can be on my own for two minutes.”

“Yes, you are an adult,” Cas acknowledges, “which is why I cannot leave you alone in the company of another known criminal.”

Dean’s jaw clenches. “Gee thanks, Cas. Tell me what you really think.”

“That’s a fact, Dean, it’s not about what I think-”

“But you didn’t have to say it like _that-”_

“How else,” Cas starts hotly, “am I supposed-”

“I don’t fucking know, just not-”

“Your demands are unreasonable.”

“Your _face_ is unreasonable.”

Sam’s eyebrows are nearly at his hairline by the time Dean ends the argument with his mic-dropping one-liner. “I’m missing something,” he says slowly.

Dean’s face twitches. Cas looks away.

Sam’s eyes narrow. “You’ve got to get me up to speed if you want this to work.”

“I don’t know what you are referring to,” Cas says stiffly.

Dean jerks his thumb in Cas’s direction. “What he said.”

“Yeah, ’cause you’re all super believable,” Sam mutters as he drags his gaze from Dean to Cas and back again.

Dean shifts in his seat.

“No,” Sam breathes, his whole face going slack, “No fucking way. You didn’t.”

“Hey-”

“Your _FBI handler?”_ Sam almost screeches.

Dean winces as Cas reddens. “I didn’t know he was FBI!”

Sam’s head whips around. “How did he not know?”

“It wasn’t deemed crucial information at the time.”

Sam full-on gapes, mouth open. “How wasn’t that crucial information?”

“He played me, Sam,” Dean interrupts bitterly. “You remember that personal project I was telling you about way back before this whole shit went down?” He waves a condescending hand across the table. “You’re looking at him.”

“Personal…?” Sam drifts off, eyes widening in a recognition. “You can’t be serious.” He rounds on Cas. “The whole time, the whole time you were negotiating with me, you were _seducing my brother?”_

“It wasn’t intentional-” Cas starts.

Sam doesn’t let him get another word out. “When I told you to approach him,” he snarls, “I didn’t mean like that! Jesus Christ, you are supposed to be better than the Lightbringer. But no, you had to _trick_ him to get him to do what you wanted. I told you, if you let me talk to him, I could flip him in a second. But no, you said you ‘had it handled’ and we had to do it ‘your way.’ Well, good fucking job.”

Dean has never been prouder.

Cas’s face contorts. “It was out of my control.”

“Big fucking deal,” Sam hisses, “you _knew_ it was wrong and you did it anyway.”

Cas’s fist pounds on the table.

Everyone in the vicinity jumps, including the Winchesters.

“I’m not doing this here,” Cas growls. “Outside. _Now.”_

He doesn’t wait to see if Sam and Dean are following before he storms out of the diner.

“I mean,” Sam says awkwardly, “you _did_ want a moment to talk without him.”

Dean slides out of the booth, shaking his head. “We’d better do as he says.”

They make their way out of the diner and out onto the parking lot in silence.

Cas looks up as the pair of them approach, his eyes flinty. “For context, I didn’t plan on seducing Dean, as he knows full well.”

Sam looks to Dean for confirmation, who shrugs.

“Yes, I know we shouldn’t have pursued Dean in this manner,” Cas continues, his expression growing darker by the word. “And it is my fault for listening to my superiors and following flawed orders. However, I want you to understand my position. It’s a family matter.”

Dean sighs. Really, fuck Cas’s family. What a load of douchebags.

“The orders came from Uriel,” Cas continues, “He’s married to Michael.”

Sam looks nonplussed, so Dean supplies, “The Deputy Director of the FBI.”

“Yes, that Michael,” Cas says impatiently as Sam’s eyes widen. “I couldn’t-” he falters for the first time, “They wield an unholy amount of influence, both at the Bureau and within my family,” he explains. “Disobeying Uriel, and by extension, Michael… was unthinkable.”

“Was?” Dean echoes.

“I’ve recently been rethinking my priorities.”

“Okay,” Sam says, brow furrowed. “So what does that mean?”

Cas shakes his head. “Unfortunately, not much at this point. Only that I am sorry for any… distress I have caused through my deception. As Dean can attest, I have been _trying_ to make up for my past actions.”

Dean runs a hand down his face. “It’s fine, okay?” he starts as Cas turns to him, his face hopeful, “Water under the bridge, like I said. You don’t need to apologize.”

“I had thought,” Cas says, his words tentative, “I could improve your situation by reuniting you and Sam.”

Dean stares at him in shock. “You thought I’d be _happier_ if you flew my brother right into the Temple of Doom?”

“He was going to come to LA anyway,” Cas says flatly, “but I figured he would be safer if it was on an FBI-sanctioned trip.”

Dean rounds on Sam. “What the hell is he talking about?”

Sam throws his hands in the air. “You’re taking down the Lightbringer, and you expected me to sit with my thumbs up my ass in South Dakota? Really?”

_“Yes!”_

Sam’s brow furrows as he turns to Cas. “How’d you know about that?”

“Charlie.”

Sam swears under his breath. “She ratted me out?”

“You were reckless and a liability to this case,” Cas maintains solid eye-contact with Sam. “Any member of Lightman's organization could have seen you while you were travelling or looking for a place to lie low. It would have ruined everything.”

Furious, Dean bites out, “I can't believe you.”

Sam's face hardens. He looks away. “Like you wouldn’t have done the same thing.”

Dean falls silent. 

If their positions were reversed, Dean _wouldn’t_ have done the same thing. He’d have booked it to California, broken into Sam’s place, and bodily hauled him as far as the road would take them.

Sam shoves his hands into his pockets once it becomes clear Dean doesn’t have an answer. “Now what?”

Cas lifts his chin. “We take down Lightman.”

* * *

At the meeting with the “wedding planner”, Dean doesn’t burst out laughing when he takes in Sam’s man bun and burgundy getup, but it’s a near call. The kid has a freaking pocket square. At least he plays a competent wedding planner. The nerd has an answer for each of Crowley’s long list of questions about the accommodations, catering, seating - everything.

That night, Dean stays homebound since Crowely is away at Roman’s place for their monthly poker night. Beer in hand (the rest of the six pack is shoved deep in the recesses of Crowley’s fridge), Dean sits on one of the pieces of artsy lawn furniture overlooking Crowley’s expansive, exquisitely pruned backyard.

Cas calls at eleven o'clock on the dot.

With his heart in his throat, Dean picks up to talk to Cas for the first time since they saw each other at the diner. He blames his mostly-gone beer as he taps the accept button. “Hey.”

“Hello, Dean,” Cas says, and Dean can hear the sheer relief in his voice. “How are you doing?”

Dean leans back in Crowley’s uncomfortable, handcrafted outdoor chair. It creaks ominously, and Dean winces. “I’m doing okay. How about you?”

“Worried about you,” Cas says frankly.

“Really? Why?”

Cas pauses. “You have to ask?”

“Uh, yeah?” Dean picks at the dog hair clinging to his slacks. “I said I’m fine.”

“And somehow I don’t believe you,” Cas says dryly. “Sam said your meeting today went well.”

“Weren’t you watching us the whole time?”

“Yes, but the cameras don’t pick up on everything. Your judgments and opinions offer an additional assessment. And,” Cas continues, hesitantly, “the last time we spoke, we didn’t end things well.”

Dean says, his voice cold, “That happens when you pitch the only family I have left into Mount Doom.” 

“I am sorry,” Cas says, and he sounds it. “I tried to mitigate the danger as much as I could.”

“Yeah, I get it,” Dean sighs. The furniture squeaks as Dean shifts more of his weight back. “Doesn’t mean I’m not still angry.”

After a beat, Cas says quietly, “I understand. It’s hardly the ideal situation by any stretch.”

Dean doesn’t respond at once, and for a moment silence falls over the line.

“Do you still want me to be your best man?” Cas asks.

Dean swallows. “Sure, if you still want to be,” he says, and the words sound only a little forced. 

“Not if it’ll put more of a strain on our relationship.”

“What relationship?” Dean asks sourly. As soon as the words are out of Dean’s mouth, the regret kicks in. He adds as a shitty explanation, “You’re still FBI and I’m still a criminal.”

“Yes, but I do consider us… friends,” Cas says delicately.

Dean can tell when he’s being handled by a pro. “Yeah, friends,” he repeats wearily. He musters up a smile Cas won’t see, but fake it ‘til you make it. “So, what’s up with you?”


	8. The Send

**Summary for the Chapter:**

> “Dean and I can share the bed,” Cas interrupts. “Sam, you can take the guest room. Nobody has to sleep on the couch.”
> 
> Dean’s mouth actually falls open. “Dude, you don’t have to do that.”
> 
> Cas shrugs, a red tinge coming over his cheeks. “My bed is bigger than the guest bed. It can fit two people more easily.”

One day at a time, Dean makes it through the month leading up to his (hopefully) last marriage ceremony. Behind the scenes, the Feds take care of the wedding planning while Michael conspicuously appears to involve Crowley in the process.

The plan hits its first snag a week and a half before the Big Day. 

Cas mentions it towards the end of their call as a warning. “Anna confirmed we have a leak,” he says grimly. “Please be extra careful about who you speak to and how you act.”

“So a regular Thursday for me.”

“I mean it, Dean,” Cas says urgently. “She found bugs in her office.”

Dean’s eyes widen, and he accidentally yanks on Growley’s leash as he stops short in his tracks. “She did?”

“They’re standard FBI-issue. Anybody with high-level clearance could have put them there.”

“Fuck.” Dean stumbles over to a park bench. Growley sniffs at Dean’s shins, so Dean picks him up to sit him on his lap. “Did they get you too?”

“No.” Cas exhales a slow breath. “The upside of being the accountant on the team, nobody thinks you say anything worth overhearing.”

“Silver linings, I guess,” Dean mutters. He absently pats Growley’s head, worrying the dark fur between his fingers. “Do you have any leads on who put them there?”

“Anna has her suspicions.”

Dean sits up on his bench, startling Growley. “Send the bugs to Charlie.”

“Excuse me?”

“Maybe she can find something you missed,” Dean says, “Or she knows somebody who knows somebody who can do it.”

“Dean,” Cas says cautiously, “this is a very sensitive matter-”

“Charlie is good people,” Dean says firmly. “She won’t rat us out. And you can’t send it to your IT guys, so you might as well go with the one lead you’ve got.”

“I suppose you’re right," Cas sighs, and Dean can practically see the defeated slump in his shoulders. "I’ll check with Anna.”

“Wait, Cas - you can trust her, right?” Dean cuts in. As Cas sucks in a loaded breath, Dean adds, “She might’ve planted them herself to throw you off the scent at the last second. The mole is running out of time - only ten days left.”

“Anna is family, Dean.”

“It’s also likely your leak is family,” Dean points out, “going by the number of your relatives swimming around the suspect pool. In fact, I would _bet_ your leak is a Novak, since this all leads back to your FBI’s Most Wanted Cousin.”

Cas audibly swallows. “I don’t like this,” he says, his voice low.

“Duh, this is back-stabbing betrayal. You’re not supposed to like it, Hamlet.”

“I meant, I don’t like choosing criminal informants over my family,” Cas clarifies.

Dean ignores the trickle of cold down his spine at Cas’s words. “Tough nuts, man,” he says. “It’s the right call.”

“I know.” 

Cas doesn't call the next day, and Dean tries not to worry. He sends a text, which does nothing to quash the anxiety churning in Dean’s gut.

 _Cas 2:03_ _  
_ _I am leaving LA temporarily, but I will be back before the wedding._

No Cas on Friday, either.

On Saturday morning, Dean video calls Charlie from Crowley’s home office while its usual occupant is still sleeping off a long night of drinking at Ninth Circle.

“Hey, Handmaiden,” Charlie waves at the screen. “What’s up?”

“Have you heard from Cas?”

“No, _Charlie it’s been so long,_ or, _How is my illustrious Queen doing today?”_

Dean rolls his eyes. “How are you, Charlie?”

“Don’t worry about it, I get it,” Charlie waves off Dean’s pitiful attempt at catching up. “You’re worried about your _dreamier_ handler.”

Dean scowls. “I haven’t heard from him in a couple of days.”

Charlie makes a face. “Neither have I. He overnighted some bugs to me and then went dark.”

Dean’s heart sinks. He ducks his head, gripping the arm rests of Crowley’s office chair to ground himself.

“But, there is good news,” Charlie says brightly. “Jo knows a guy who can crack these little suckers.”

Dean’s head snaps up. “She does?”

“Yeah, in her pre-Lightbringer days,” Charlie says, a small smile spreading across her face. “She ran a crew with this genius MIT dropout.”

“Genius?” Dean whistles. “From you? High praise.”

Charlie shrugs. “I’m way cuter. How has nobody told him mullets went out of fashion decades ago?”

“Maybe they’re scared of him.”

Charlie chokes. “Unlikely,” she snorts. “Ash is, like, the least intimidating guy I’ve ever met. And I remember Garth.”

Dean smiles despite himself. “So what’d he find?”

“Nothing yet,” Charlie says, “We did the handoff yesterday - under _our_ handler’s nose, in a fucking safe house, while under house arrest. It was like Ocean’s Three up in here.”

Dean groans.

“Cheer up,” Charlie says bracingly, “Ash thinks he’ll get the info to us in a couple of days.”

“We don’t have a couple of days,” Dean growls. “I’m getting married in six.”

Charlie’s brows draw together in concern. “It’ll be okay, Dean.”

Dean just shakes his head. “You can’t bullshit me.”

Charlie rolls her eyes. “It’s not bullshit,” she says. “We’ll get this info to you or Cas in two days - that gives you four more days to figure out what to do. You’ve always told me you worked best while thinking on your feet, anyway.”

She’s not wrong. “Fine, but if everything goes sideways, I’m blaming you, Bradbury.”

“This isn’t the Red Wedding II,” Charlie rolls her eyes. “If things go wrong, Cas has your back.”

“If he’s not dead already.”

“He’s not.”

“You sure about that?”

Charlie nods. “Anna texted Naomi Novak, mentioned she had dinner with him last night.”

Dean nealy sags in relief. “You hacked her phone?”

“I hack everyone’s phone.” Charlie waves her hand. “She’s not special.”

“Why would he stop talking to me, though?” Dean asks, half to himself.

“Well, he flew to Virginia to visit the Novak estate two days ago,” Charlie says slowly. “So I’m guessing he’s worried about being spied on. Heh,” she chuckles, “ironic isn’t it? Spies spying on spies?”

Dean blinks. “The estate where he grew up?”

“Michael and Uriel Novak live there now,” Charlie explains. “Zachariah and Naomi are frequent guests too.”

“So... all the FBI elite in one place,” Dean surmises.

“Uh huh,” Charlie agrees. “The old Milton estate - bigger, but farther from DC - is a few miles away. It’s technically Raphael's, but he mostly stays at his townhouse.”

Dean sighs. “So Cas suspects one of them.”

“Probably.”

* * *

The day before the ceremony, Dean has a tradition. He takes care of any last-minute marriage crap in the morning. At noon, Dean, his handler, and whoever else is working the job with him, go to a fancy hotel room, drink just enough to not get hungover the next morning, and order the most expensive thing on the room service menu. Plus a crap ton of french fries in case the real food sucks.

Twenty-four hours before his wedding to Crowley, Dean is painfully sober and painfully lacking in the french fry department.

Instead, he’s holed up in FBI quarters with Sam, Milton, and Balthazar, running worst-case scenarios. 

Nothing like predictions of murder and mayhem to get him in the celebratory spirit.

By noon, Dean would give his left hand for one of those tiny bottles of vodka from the hotel minibar. He slumps over the table. “Please tell me there’s a bachelor party in it for me after all this.”

“Are you still a bachelor after taking your seventh spouse?” Balthazar muses, tapping his finger against his chin. 

“Bite me,” Dean says darkly.

“Dean,” Sam says reproachfully, “Come on. This is partially for your safety. Don’t you want to be prepared?”

Dean sits back up, scowling. “Is Lightman really likely to have a helicopter waiting as a getaway car?”

Milton purses her lips, her gaze darting to Balthazar before landing back on Dean’s face. “I admit, that one is one of the less plausible exit strategies.”

Balthazar smirks. “I would like to hear more about how you would jump for the helicopter to hold it down.”

“Dude,” Dean scowls, “it’s from Captain America. Do you guys sleep in pods in the basement or something? How could you not know that?”

“My tastes veer more towards more tasteful cinema.”

“Uh huh,” Dean nods, distinctly unimpressed. “Cas told me you saw Titanic five times.”

Milton shuffles her papers around, hiding her small smile.

“They were hate-watches,” Balthazar sniffs.

Dean crosses his arms across his chest. “That movie is as long as fuck. You can hate-watch for fifteen hours?”

“We’re getting off track,” Milton cuts in before Balthazar can muster a comeback. “Should we have a short break before the next one?”

Balthazar leaves the room muttering about Kate Winslet.

Dean turns back to Milton as she keeps tapping serenely away on her tablet. “You’re staying here?”

Milton shrugs. “I’m supposed to be watching Sam,” she says, tipping her head in his direction. “If you want to talk, don’t mind me.”

Sam rolls his eyes.

“Talk about a short leash,” Dean says, frowning. “Can he go to the bathroom by himself too?”

Milton’s gaze turns steely. “One more day, Dean. That’s all we ask. If we catch Lightman tomorrow, then you’ll be as good as a free man. Until then, _don’t test me.”_

Dean blinks. “Yeah, sure,” he says, chastened.

Sam snorts. “If you wanna get some air, I’m good here.”

“Okay,” Dean says slowly, “If you’re sure.”

He leaves the conference room and takes off in a random direction. Almost subconsciously, his feet take him to Cas’s empty office. He pushes on the door, half-expecting it to be locked. But it isn’t.

He fiddles with his phone in his pocket before he gives in to temptation.

The call picks up as he closes Cas’s office door behind him.

“Dean?” Cas asks, his voice sounding urgent and grateful all at once. A crowd of people carrying on their own conversations burble in the background.

Dean sinks down onto the chair opposite Cas’s desk. “Hey, Cas,” he says, more relieved than he’d ever say. “I didn’t think you’d actually answer.”

“I just landed in LAX,” Cas says before thanking someone on the other end.

“The big shindig is tomorrow. Cutting it a little close, aren’t you?” Dean asks, forcing lightness into his tone.

“You have no idea,” Cas says darkly.

Dean straightens in his seat, his joking attitude evaporating. “What’s up?”

“I found the mole.”

Dean’s mouth falls open. _“What?_ Why didn’t- _”_

“I don’t know who he’s working with.”

Dean’s shoulders slump as he asks grimly, “He’s family, isn’t he?”

“Yes,” Cas says before apologizing to someone at the airport.

Dean inhales a slow breath as he tries to sort out his thoughts. “What do we do?”

“I’m still trying to figure that out. Where are you, anyway?”

“I’m at the FBI-”

Cas swears loudly on the other end of the line. “I’m going to be there in fifteen minutes - as soon as I find my way out of this goddamned airport.”

“Woah, hey,” Dean says quickly, “What’s going on? Are Balthazar and Milton in on it? We’ve been with them all day.”

“I don’t know,” Cas says, and Dean has never heard him sound so frazzled. “It’s all been happening so quickly.” He cuts himself off with a quick retort to someone else.

“Talk to me,” Dean says, almost pleading, “What is going on, Cas?”

“I can’t tell you over the phone,” Cas says infuriatingly, “especially if you're at the FBI. I’m almost at the parking garage - I’ll pick you and Sam up in fifteen minutes. Maybe sooner. Do exactly what Milton and Balthazar tell you until I get there - it’s in their best interest to keep you both alive until tomorrow, no matter where their allegiances lie.”

“Cas-”

The line goes dead.

Dean barely keeps himself from taking Cas’s desktop computer and throwing it out the tinted windows.

* * *

Cas bustles Dean and Sam out of the FBI mothership in record time over Milton and Balthazar’s protests.

Safely in the Lincoln, Dean waits for Cas to start the engine and merge onto the main highway before he asks in a casual voice, “So, mind telling us what the fuck is going on?”

“Uriel is working with Lightman,” Cas says shortly.

Dean’s mouth falls open. “Uriel, your boss?”

Sam’s face goes slack. “The Deputy Director’s husband?”

“Yes, that Uriel,” Cas says impatiently.

Dean whistles.

“How do you know?” Sam asks.

“Miss Harvelle’s contact was able to trace the bugs and hack into the audio they recorded.”

Sam runs a hand through his too-long hair. “Who else is in on it?”

“Potentially anyone in my unit,” Cas says grimly. “Uriel directly oversees about fifteen agents. Indirectly - who knows who else he involved.”

Dean finally unsticks his tongue from the roof of his mouth. “So they know about our plan. Are we calling the whole thing off?”

Cas flips on his blinker before carefully taking his exit. “I don’t know.”

“You don’t know?” Dean repeats incredulously.

Cas shakes his head jerkily. “There are many factors to consider.”

Dean scowls. “Such as?” he prompts through gritted teeth. 

Cas’s forehead pinches. “Whether we can ensure your safety, for one.”

Sam’s mouth opens, but Dean beats him to the punch. “Forget about that for a second. Will Lightman even show?”

Cas exhales a long breath. “Yes, he’s always been absurdly confident, and he would never miss the opportunity to taunt us.” He turns to Dean as they pause at a red light. “But, Dean, you know how sadistic he can be. And Uriel can be ruthless with his targets - he has killed before in the name of the law.”

Dean stares grimly straight ahead. “So?”

Sam kicks the back of his seat. “Dean!”

“Think about it,” Dean says, twisting around to get both of them in view. “Say we sit this one out. What'll we do next? Stay holed up in South Dakota until the next blue moon when Lightman creeps out of hiding?” He narrows his eyes at Sam. “You barely made it four months before making an escape plan.”

Sam’s mouth purses. “I won't risk your life, Dean.”

“Neither will I,” Cas says stonily.

Dean stares out the windshield, jaw clenched. “Dammit, Cas, you can’t babysit us forever.”

A fleeting expression on Cas’s face says _watch me,_ but it’s quickly replaced by a look of resignation. “No, I can’t,” he admits quietly. 

“Whatever we do,” Sam says into the silence, “it needs to be more than just us. Three people up against Lightman and Uriel isn't going to cut it.”

“I believe Charlie is on it,” Cas says, his brow creasing. “I told her to start with Bal and Anna first. But she said it might take some time to clear them.”

“Great,” Dean mutters.

* * *

They spend the rest of the afternoon on yet more contingency plans. Plans without Milton. Plans with Milton. Plans without Balthazar. Plans with Balthazar. Plans with fifteen agents. Plans with only one agent. 

Dean’s head is spinning and he’s feeling vaguely nauseated by the time their Chinese takeout arrives.

Sam hogs the dumplings because he has no respect for his elders, and Cas zeroes in on the noodles. Dean manages a half dozen bites of chicken before he gives up.

To give them all a mental break, Cas puts on some mindless sitcom while they eat. Dinner passes with very little conversation even though none of them are really invested in Pawnee’s Harvest Festival.

They all make a mutual decision to turn in early, even Cas, to Dean’s infinite surprise.

“I’ll take the couch,” Sam offers as the three of them stare at the two bedroom doors.

Dean waves the offer away. “Fuck that, you’re too tall. I can manage. Not like I’ll be sleeping much anyway.”

Cas glares at the pair of them. “I’ll take the couch. You are both guests.”

Dean gapes. “I’m not gonna make you sleep on your own couch.”

“Dean and I can decide who gets the bed,” Sam proposes. He lifts a tentative fist in Dean’s direction.

“No way.” Dean slashes his hand through the air. “No fucking rock, paper, scissors. You always cheat.”

“It’s not cheating if you always pick-”

“We’ll flip a coin or some-” 

“Dean and I can share the bed,” Cas interrupts. “Sam, you can take the guest room. Nobody has to sleep on the couch.”

Dean’s mouth actually falls open. “Dude, you don’t have to do that.”

Cas shakes his head, reddening slightly. “My bed is bigger than the guest bed. It can fit two people more easily.”

Dean shares a look with Sam, who shrugs. Dean tries not to let the flare of excitement show on his face. If it’s gonna be his last night on Earth, he’s gonna fucking take what he can get.

He follows Cas out of the living room. Cas's bedroom holds a few more personal touches than the rest of the apartment - a decently-sized family portrait full of strained smiles sits on top of Cas’s dresser, and a couple of dust-covered novels are stacked on Cas’s bedside table. But the crowning glory is Cas’s king sized bed, occupying a good chunk of the floor space. 

Cas rubs the back of his neck as he watches Dean. “I know the bed seems like an extravagance for one man, but I have such a hard time sleeping, I felt the need to splurge.”

“I get it,” Dean says, a touch awkwardly. “The only thing I always asked for on the jobs was a memory foam mattress - or a topper, at least.”

Cas nods solemnly. “A good night’s sleep can make any morning seem less daunting.”

Dean sighs as he sinks down on Cas’s bed. “Are you going to be OK tomorrow?”

Cas sits next to him. “I feel like I should be the one asking you that.”

“I’m not the one arresting family.”

Cas slumps forward, bracing both elbows on his knees. “Something has always been broken in my family,” he says in a low voice, “We don’t - we’re not made right. It’s taken me a long while to see it, but it’s true. This has probably been a long time coming.”

Dean almost reaches out to pat him reassuringly on the shoulder, but he snatches his hand back before Cas notices. Instead, he stares straight ahead at the unremarkable off-white wall. “I think you’re alright.”

Cas turns to him. “You do?”

Dean swallows. “For what it’s worth, yeah. You always try to do the right thing. You took a chance on me, even though it could have blown up in your face. You do a job you hate because you think it’ll help people.”

“I don’t hate my job,” Cas protests quietly.

“You don’t?” Dean asks, eyebrows raised.

Cas lifts his shoulder in a half-shrug. “I suppose it’s a case of too much of a good thing. For a long time, I thought the job was all I had.”

“And now?”

“I’m coming around to other things that could occupy my time.” One corner of Cas’s mouth ticks up in a lopsided smile. “Cooking, for one.”

Dean takes a chance and bumps his shoulder against Cas’s. “Just make sure you have a working fire extinguisher in the house.”

Cas smiles. “Friends, for another.”

Dean’s mouth goes dry. “Yeah?”

Cas ducks his head. “If it’s not too much of an imposition.”

Dean snorts. “Of course not. In case you hadn’t noticed, I’m a little short in the friends department myself. Hazards of the job, I guess.”

“I can sympathize.”

Dean gets to his feet before he can do something stupid like lean over and kiss Cas until he can’t breathe. He jerks his head towards the bathroom. “I’m gonna…” he drifts off.

Cas licks his lips. “Of course,” he says, his tone carefully level, “If you don’t mind, I’ll get changed in here and then use the bathroom.”

“Fine with me,” Dean says before he grabs his overnight bag and leaves - flees - for the safety of the bathroom.

The click of the door closing behind him has never been more satisfying. He quickly strips and resists the urge to inspect himself in the mirror for too long. Cas knows what he fucking looks like - and it’s not like one night will suddenly change Cas’s mind and he’ll realize Dean is a hot piece of ass who deserves to get fucked six ways from Sunday.

Cas is only making the best of a bad situation. Like he has been since Dean chose him in that coffee shop.

Dean knocks on the door. “You decent?”

“Yes, Dean.”

With a sharp inhale to brace himself for whatever waits on the other side, Dean opens the door. 

First of all, Cas’s definition of decent is very different from Dean’s. He’s clad in flannel pajama pants, and they’re _doing things_ to Dean. Maybe because he’s such a flannel hog himself, so it’s almost like Cas is wearing _his_ clothes. He’s almost positive he has a shirt in the same color and pattern. And where the fuck is Cas’s shirt?

“Missing a top half there, buddy,” Dean says in a strangled voice.

“My apologies.” Cas pulls open a drawer and grabs a plain white tee shirt. “I usually don’t wear one -” just shoot Dean now with his FBI-issued firearm and be done with it “-so I was having a hard time deciding.”

“Forget it,” Dean says because he’s already going to hell, so he might as well enjoy the trip down. “It’s bad enough you have to deal with me sharing your space. Dress how you want to.”

Cas casts a long look at the shirt in his hands. “I don’t want to make you uncomfortable.”

“Impossible,” Dean mutters under his breath.

“Excuse me?”

“It’s impossible,” he says in a louder voice. He forces a grin. “Shameless, remember?”

Cas’s conflicted expression softens. “We both know that’s not true.”

“Seriously,” Dean sighs, “It doesn’t matter.”

“If you insist.” Cas drops the shirt back in the drawer and stands by the bed. “Which side would you like?”

“Doesn’t matter,” Dean repeats.

Cas shakes his head. “You can ask for things for yourself,” he says plainly.

Dean frowns. Their conversation is running along eerily similar lines as a talk Crowley had with Michael. “It’s really fine,” he dismisses, “I don’t care what side I sleep on. I can really get my four hours anywhere.”

Cas’s eyes narrow. “I’m not talking about the bed.”

Dean runs a hand through his still-wet hair. “Then what the fuck are you talking about?” he asks wearily.

“Sit down first.”

“Right,” Dean says dubiously. He takes the closest side because it really _doesn’t fucking matter._

Cas takes a step towards him, thinks better of it, and walks around to the other side of the bed. “I’m talking about your life after Lightman. You’ll need to decide what you want to do.”

Dean doesn’t mention the non-zero chance he won’t be around to make decisions. He says carefully, “I assume I’ll be in wit-sec and contributing to the prosecution.”

“And after?”

Dean sighs. “Not sure. If tomorrow doesn’t go tits up, I’ll have a couple of years to figure it out.”

“But what would you _want_ to do?” Cas presses, “If you could do anything?”

Dean screws up his face. “Do we really have to do this now? I’ve got no fucking clue, Cas. This,” he makes a wide gesture with his hands, “has been my life for the past decade. I only ever started thinking I’d get out of it a couple of months ago. I need more time.”

Cas swallows and sits back against the pillows. “Yes, Dean, of course. I’m sorry.”

Dean doesn’t look at him, can’t see the look on Cas’s face. “Don’t feel sorry for me. I made my bed. And Sammy’s already agreed to stay out of the line of fire tomorrow to run coms, so that’s all good.”

Dean nearly jumps out of his skin at the first touch of Cas’s hand against his.

“Very well,” Cas says. He gives a small squeeze of reassurance before retreating. Dean’s hand burns, and he misses the touch of Cas’s warm skin like an amputated limb.

“I won’t force the issue,” Cas continues, “but you should give some thought to what you really want out of life.”

Dean keeps his mouth firmly shut, almost grinding his teeth together to keep the _“_ _you”_ to himself. Instead, he busies himself with getting ready for bed. 

The bed is enormous. It could easily fit three people, maybe four if everyone was okay with a little squeeze. Dean sticks to his side, turned to face the opposite direction, because he’s not an idiot. Cas does the same.

Still, Dean feels the heat from Cas’s body all along his back. Logically, it’s impossible with the size of Cas’s orgy bed, but Dean can’t help imagining Cas right behind him, just out of reach. 

And isn’t that his life.

* * *

In the morning, Dean wakes up to an empty bed. He lays there, wrestling with his mingled relief and disappointment. Cas’s side of the bed is cold, and there’s no sign of him in the bedroom or attached bathroom. He’s probably been up for hours, working, since today is D-Day and nobody has time to mope around.

When Dean emerges from the bedroom, he finds Sam and Cas already in the kitchen. A half-depleted stack of pancakes sits between them.

Cas wastes no time in shoving a mug of coffee into Dean’s hands and telling him Charlie cleared Balthazar and Milton last night. Apparently he’s been up since four-thirty, finalizing all their plans now they have a solid team. 

Cas has a slightly manic energy about him, and Sam looks like he slept maybe ten minutes total. Dean half-heartedly munches on a pancake. 

Dean’s been driven to his wedding seven times now. But he’s never had nerves like this before. It feels like he’s going to vibrate out of his skin, and his brain can hardly dwell on one pants-shitting scenario before another one takes its place. He takes deep, calming breaths the whole way.

At the church, Cas flits around like a restless bird. He checks the perimeter. He double-checks the perimeter. He tests their private surveillance cameras. He tests the FBI’s surveillance cameras. Dean manages to stop him from combing the pews with a metal detector, but barely.

An hour before the ceremony, Dean takes a call from Crowley. His eyes follow Cas the whole time as he spins some BS about not getting cold feet. When he gets off the phone, he all but drags Cas by the arm to a nearby alcove, out of sight of the rest of the agents milling around the church. “Level with me,” Dean says seriously, “You don’t seem OK.”

Cas glares. “I’m fine.”

Dean takes a small step back, hand open and fingers spread. “All this freaking out you’re doing? It’s burning you at both ends.”

Cas bristles at the accusation. “I’m not freaking out.”

Dean’s eyes narrow. “You asked me three times in five minutes if Crowley was on his way.”

“Is he?”

“He is, but that’s not the point, Cas. I get this is stressful, and you’re up to your ears in things to do. But you gotta calm down.”

Cas squints at him like Dean’s speaking ancient Greek. He says slowly, like Dean’s hard of hearing or particularly dense, “This is the biggest case of my career.”

“And you’re going to blow it if you spend all your energy now,” Dean says bluntly. He scans the agent-free area around them before. “I get it. I used to go nuts before big jobs. I’d plan everything to a T, rehearse lines, the whole shebang-”

Cas crosses his arms across his chest. “I’m guessing this anecdote doesn't end well.”

“-I’d be so worn down by game time,” Dean continues over Cas’s interruption, “I couldn’t tell which way was up. Forget being suave, or charming, or whatever. I was lucky if I could remember their name.”

“You’re exaggerating.”

Dean purses his lips. “A little. I’d never forget a mark’s name. But I’d fuck up my backstory or something else. Bottom line, if you wind up too stuck in your own head, you won’t see what’s right in front of your nose.”

“Like what?”

“Jesus Christ,” Dean mutters under his breath. He says, louder, “Like, you can do this without freaking the fuck out.”

Cas blinks.

“You’re good at this, Cas.” Dean reaches out to squeeze his shoulder. “I’ve told you before, you can trust your instincts. You don’t need to drive yourself crazy worrying about every little thing.”

“What if something goes wrong?”

“Something always goes wrong,” Dean says wryly as he lets go. “That’s why you gotta be quick on your feet.”

Cas cuts in, “Or I could plan for contingencies.”

“You can’t plan for every single contingency, man,” Dean says flatly. When Cas still doesn’t look convinced, Dean tries, “What about me, huh?”

Cas tilts his head. “What about you?”

Dean looks away. “You didn’t plan on me falling for you, but you rolled with the punches just fine,” he says, ignoring the embarrassment, regret, and heartache bubbling below the surface, “and strung me along like a pro. Hell, you even got me to sign up for this whole thing that should logically send me running for the hills.” He gestures ruefully at the sanctuary around them.

“That wasn’t all me.”

Dean shrugs. “Most of it. Wasn’t like I was going on any dates with any other nerdy secret agents.”

Cas shakes his head. “No, I mean I couldn’t have done any of it without you.”

Dean barely holds in his snort of derision. “Sure, every con needs a mark, but-”

“You misunderstand me,” Cas says over the rest of his words. “You - your intelligence, your insight, your _caring_ \- were what tipped the scales in our favor. You took that initial risk when we first met - I merely followed your lead.”

Dean’s mouth falls open as he struggles to respond. “Dude.”

Cas's face is impossibly open as he says, “That’s what drew me to you in the first place.”

“You were drawn to me?” Dean repeats slowly, as if waiting for Cas to correct him with every word.

But Cas nods in agreement. “You’re like no one I’ve ever met.”

Dean, equally uncomfortable and pleased, can only mutter a lame-ass, “Yeah, well, you’re awesome too.”

Cas swallows, his eyes a little wide. “Look, Dean,” he starts. He unwinds his arms and shoves his hands in his coat pockets instead. “After this is all over, I was wondering if we could talk.”

Dean makes a face. “Why the wait? We’ve got a little downtime since I’m not gonna let you bother Milton about the perimeter again.”

Cas shakes his head. “Not now, the day’s events might influence your decision.”

Dean’s mouth opens to demand Cas to spill the beans, but some agents call Cas’s name.

Cas reaches out to grasp Dean’s forearm. “Promise you’ll find me when this is all over,” he says, the pads of his fingers digging in. “Promise me, Dean.”

Dean’s eyes flick to the agents before landing back on Cas. “You got it.”

“Good,” Cas breathes before he turns around. “Agents Benjamin and Mirabel, what can I do for you?”

* * *

Thirty minutes to go, and Dean gets shuffled backstage out of sight. Guests, both Crowley’s and the actors the FBI hired to play Michael’s, have started to arrive.

He kills as much time as he can playing stupid games on his phone, rehearsing the plan in his head, and texting Sam, stationed in one of the FBI vans across the street. 

He gets suited up - and goddamn, does Dean hate the monkey suit. He gels down his hair and tries not to let his fear show on his face. Nerves are okay for a wedding. Blatant terror is not.

Ten minutes before showtime, Cas slides into the room holding a bulky black shape in front of him - a bulletproof vest. “Hello, Dean.”

“Hey, Cas.” Dean takes a curious step forward. “What’s up? Should I head out?”

Cas shakes his head and thrusts the vest at Dean. “Here, put this on.”

Dean doesn’t move to take it. “Why?” he asks, suspicious.

“Why do you think?” Cas snarks back.

Dean’s eyes narrow as he takes in Cas’s suit, noticeably baggier around the midriff than a half hour ago. “Is that yours?” he asks pointedly. 

“No,” Cas lies, bald-faced and terrible, as usual.

Dean purses his lips. “I’m not taking your vest, man. It could save your life.”

“It could save yours.” Cas shoves the vest at Dean. “Take it.”

“No.”

“Dean,” Cas says, a warning tone in his voice.

“It’s not even gonna fit me,” Dean protests. “This tux is tailored.”

Cas reaches in his pocket and withdraws the tiniest pair of scissors Dean has ever seen. The blades are about the length of his little finger.

“You can’t be serious,” Dean says faintly.

“Deadly,” Cas growls as he takes the vest back and stands in front of Dean like an immovable boulder. “I’ll help adjust your shirt if you take your jacket off.”

Dean takes a step back. “No fucking way. I know you’re worried about me and whatever, but you gotta look after yourself. You’re going to need the vest.”

“I can protect myself,” Cas says mulishly.

Dean smirks, schooling his fear away from his face. “Being a stubborn dumbass doesn’t protect against flying bullets, Rambo.”

“Neither does being a self-sacrificing martyr,” Cas retorts.

“I’m not sacrificing anything,” Dean protests, not exactly truthfully. “Who knows if they’ll even bring guns?”

“This is America,” Cas growls, and point taken. “Take the goddamn vest, Dean.”

Dean crosses his arms across his chest, unpleasantly reminded of Sam refusing to eat marshmallow fluff-covered mac and cheese. “No.”

“You are insufferable,” Cas declares.

“I know,” Dean says as calmly as he can. He glances at his watch. “Put the vest back on, and I’ll meet you outside in five. We’re almost running out of time.”

Cas shakes his head. “I’m not leaving until you put this on.”

“Why not? Why is this so important to you?” Dean demands. He throws his hands in the air. “Look at the facts, Sherlock. I’m a high school dropout with about six legitimately earned dollars to his name. If I come out of the other side of this, I’ll probably be WitSec for the rest of my life. But you,” Dean goes on, “You’re about to make the biggest bust of your career. You have a family that supports you - not the dickbag parts, obviously - and a good life ahead.”

Cas’s expression falls. “Dean,” he says, and Dean’s heart breaks with the way he says his name, filled with pity and guilt.

“Drop it,” Dean says brusquely. “Wear the vest. Take down the bad guy. Save the day.” 

Cas, the stupid son of a bitch, doesn’t do as he’s told. He strides forward, a determined look on his face.

Dean braces for impact. Hopefully Cas won’t get his good side. He's about to get married, after all.

But instead of a fist to his cheek, Dean gets the soft press of lips to his own.

Shocked, Dean hardly has time to savor Cas’s kiss before Cas pulls away. He shoves the vest against Dean’s chest, and Dean’s hands automatically reach up to keep it from falling to the floor.

“If you have ever felt anything for me,” Cas says, his blue eyes boring into Dean’s, “Anything at all, wear it - for me.”

Dean stands there, a useless mannequin in a tailored tux, and Cas leaves.

**Notes for the Chapter:**

> Last chapter up on Friday!


	9. The Blow Off

**Summary for the Chapter:**

> Crowley waits expectantly for him at the end of the aisle, but Dean only has eyes for Cas.

**Notes for the Chapter:**

> _With a thousand lies  
>  And a good disguise  
> Hit 'em right between the eyes  
> Hit 'em right between the eyes  
> When you walk away  
> Nothing more to say  
> See the lightning in your eyes  
> See 'em running for their lives_
> 
> \- You're Gonna Go Far, Kid by the Offspring

Pachelbel’s Canon can go fuck itself. For once, couldn’t Dean walk down the aisle to some good tunes? His best marriage ceremony was to Pam at the courthouse. They rode back to her place to the sound of Def Leppard and REO Speedwagon.

With measured steps and a fake-ass smile, he walks in time to the music. The sanctuary is beautifully decorated with brilliantly white flowers (mostly to obscure the cameras). Sunlight streams in from the large stained-glass windows, throwing the assembled agents, actors, and bankers under a kaleidoscope of color.

Crowley waits expectantly for him at the end of the aisle, but Dean only has eyes for Cas. He stands on the other side of Ishim, slightly out of the way and looking not at all bothered by the complete tailspin he sent Dean into five minutes ago.

By the time Dean recovered, he hardly had time to change into the goddamn vest.

At the altar, Dean carefully trains his gaze away from Cas and turns to face Crowley. He ignores Milton and Balthazar’s occasional observations murmuring in his ear piece.

Ishim starts, “We are gathered here today to join in holy matrimony. It is a blessed way of life-”

Dean tunes him out.

How _dare_ Cas. Weren’t they past using Dean’s feelings against him? Dean was only looking out for the idiot. Cas has to know if anything happened to him, Dean would never forgive himself. What a cheap fucking trick. 

Someone, probably Cas, pokes him hard in the back.

Dean startles and snaps to attention. Ishim is still droning on about the blessings of marriage. Dean can’t relate - it’s not like he ever stuck around long enough to find out.

“Marriage is the covenant by which two people establish between themselves for their whole lives,” Ishim intones gravely. “This partnership is based on love, devotion, and trust-”

Inches away from his right ear, Cas shouts, “Get down!”

Dean is shoved, hard. He stumbles. Pain explodes against his left side. Gasping, he falls the rest of the way to the ground. He clutches at his ribs, half expecting for his hand to come away tacky with blood.

But the vest.

Above him, Crowley yells, “He’s got a gun!”

Dean scrambles for cover, hiding behind the first row of pews. He inhales a shuddering breath, trying to breathe through the pain as Lisa taught him. He raises his head.

Agents have drawn their guns. Actors and financiers are scrambling out of the church.

An agent has the shooter subdued in a half-nelson, his face shoved the back of a pew - Edgar, Dick Roman’s fixer.

It takes a moment to register the voices shouting Dean’s his ear.

Cas scans the crowd. “Agent Flagstaff has the shooter.” He raises his gun higher. “No sign of Lucifer.”

Balthazar’s voice comes through Dean’s earpiece, “No sign of him at the back entrance either.”

“Fuck,” Milton swears. “I didn’t catch him in the crowds at the front.”

“Uh, guys,” a new voice comes through, and Dean nearly has a heart attack. “I think I got him.”

Cas barks, “Sam?”

“Yeah, I’m in the parking lot across the street - _shit,_ give up already. Come soon, he’s not easy to hold down.”

“I’m on my way,” Balthazar reports.

Dean sucks in a deep breath. His side aches as it presses against the restrictive vest, and he grimaces.

“Dean?” Cas crouches next to him, eyes filled with concern. “Are you okay?”

“What, not going to say, ‘I told you so’?” Dean manages weakly.

“Not right now.” Cas straightens and offers Dean a hand up. His face falls as Dean staggers to his feet. “ _Are_ you OK?” he repeats.

“I just got shot,” Dean says harshly. He looks around, but there’s no sign of Crowley. Only a half-dozen agents roam, alert, through the sanctuary. “What do you think?”

Cas ducks his head. “My apologies. That was a stupid question.”

Dean sighs. “No, it wasn’t. I’m not bleeding out, so that’s good.”

Cas only gives him a tight-lipped nod as they make their way towards the entrance. Through their earpieces, they hear Balthazar taking custody of Lucifer from Sam. They make it outside without much hassle, although Dean has to lean against Cas as they make it across the street.

“I saw Lilith’s car,” Sam says, a little breathless as he watches Balthazar lead Lucifer away. “And I just… waited by it. Well,” he shrugs, “after I removed a couple parts of the engine. You know, as a precaution.”

“Of course,” Cas says, his expression slightly dazed. “A precaution.”

“His gun’s over there,” Sam says to Milton, who strides over to inspect it. “I heard a gunshot in the church, and then everything exploded. What happened? I couldn’t see from over here.”

“Dick shot me,” Dean says. “Or had me shot. Or something.”

Sam’s whole body spasms as his arms make an aborted attempt to reach for Dean. _“What?”_ he chokes out. 

Dean prods the bullet hole in his tux with his fingertip. “I’m fine. Hurt like a mother even under the bulletproof vest.”

“You had a vest,” Sam says, sagging with relief.

“Cas made me put it on,” Dean says, grimacing.

Cas nods. “I told you so.”

Dean snorts, hissing as his ribs protest against any form of laughter.

Sam only looks slightly less concerned. “You’re really fine?”

“Really,” Dean assures.

“So what now?” Sam asks as he glances around.

“Now,” Cas says, “I have to help clean up the scene and fill out paperwork.”

“Oh,” Sam says, disappointed.

“An agent can drop you and Dean off at my apartment, though,” Cas says as he nods at Agent Samandriel, who bounds over at once. Cas turns back to them. “Unless you’d rather stay at the FBI quarters.”

Sam turns to Dean, who shakes his head. “No,” he speaks for the pair of them, “We’ll crash at your place.”

* * *

Dean leaves Cas’s bulletproof vest on his bed, slaps some ice on the bruise on his side, and goes practically comatose in front of recorded episodes of Jeopardy! Cas thoughtfully saved for him. His adrenaline crash in the late afternoon means he naps on the couch until dinner.

All he has to do is look at Sam, sitting at the other end of the sofa. Sam’s single headshake is enough to tell him Cas isn’t home yet. Dean lets his eyes drift closed again.

He wakes up to hushed whispers.

“Dean?” Cas asks. A dark shape turns to him, backlit by the Jeopardy! board, “Are you awake?”

“Now I am,” Dean grumbles as he rubs his eyes with his fist and blinks around blearily. “What time izzit?”

“Almost ten,” Cas says. “I had dinner at the office, and Sam apparently ate a few hours ago. Are you hungry? Or would you like to sleep on a real bed?”

“Food,” Dean sits up, “and coffee. Lots of coffee.”

“It’s pretty late for caffeine,” Sam says skeptically.

“Bite me,” Dean says without any heat.

“I’ll get you some water,” Cas says, eyeing him critically. “Maybe you’re dehydrated.”

“Yeah, fine, and after that, coffee!” Dean calls as Cas steps away. He turns to Sam. “What’ve you been up to?”

Sam shrugs. “Not much. Debriefed Charlie and Jo on what went down. They say hi. Jo says good job on not dying. I caught up on some Netflix.”

Dean stumbles to his feet and flips on the overhead light. Sam winces. “There,” he says as he flops back down on the sofa. He twists around to see Cas approach, holding three beer bottles and a glass of water in the other.

“There was a party at the office,” Cas murmurs as he sets his bounty down on the coffee table. He reaches inside his pocket for the bottle opener and silently hands Dean and Sam a drink before uncapping his own. He perches awkwardly on the arm of the sofa since there’s not enough room for a third person. “But I missed most of it due to paperwork.”

Dean claps him on the back. “Happy to be your backup party, man.” He takes a long pull of his beer.

Sam tips his back. “Cheers, Cas.”

“Yes, um,” Cas leans over and belatedly raises his bottle, “to us.”

Dean smirks as he raises his too. “To taking down Lightman,” he toasts.

“Long may he rot in prison,” Sam adds as he clinks them all together.

They drink in silence.

Sam speaks first. “So what’s happening with Uriel?”

“He’s in custody,” Cas says, expression hardening. “I’ve heard Michael has already drafted divorce papers.”

Dean snorts. “It’s been like six hours. He’s not going to give him the benefit of the doubt?”

Cas shakes his head. “Michael’s judgments tend to be final. He’s not one for mercy.”

Dean whistles. “And Crowley?”

Cas’s face is unreadable as he turns to Dean. “The evidence you collected was enough to detain him on formal charges. If you’d like to visit him - I, ah, know you were close-”

“For the con, Cas,” Dean says sharply. “I’m happy right where I am, thanks.”

“He’s asked for you,” Cas says quietly.

Dean pales, and he has to throw back a large gulp of beer to get his feet back under him. “I’ll think about it, okay? I don’t want to see him right now, that’s for sure.”

“Of course.”

Sam looks at the pair of them, his eyes shrewd. “And the guy who shot Dean?”

Cas frowns. “Edgar Simmons is out on bail. His lawyer is… formidable.”

Dean tips back his drink. “Yeah, they’re all slippery bastards.”

“But why’d he shoot Dean?” Sam asks.

“Dean was the most prominent loose end, from Lucifer's perspective. If Dean died under our protection, it would sour our relationship - yours and mine,” Cas says with a meaningful glance at Sam, “And Jo Harvelle and Charlie Bradbury would probably follow suit. We think he contacted Roman through a third party and spun some tale about Dean distracting Crowley from his work at the firm.”

Dean’s mouth falls open. “That’s all it took for Dick to get on board with murdering me?” He snorts and shakes his head. _“Dick.”_

“We also think a hefty bribe was involved.” Cas nudges Dean’s abandoned glass of water closer. “You should still hydrate. Alcohol-”

“Yeah, I hear you,” Dean mutters as he picks up the water and takes a sip.

Cas nods, satisfied.

Sam rolls his eyes. He chugs half his beer before handing it to Dean. “I’m gonna hit the hay. You two,” his gaze flits between the pair of them before he gets to his feet, “do whatever you’re gonna do. Just don’t wake me up.”

“Sure thing, Sleeping Beauty,” Dean calls to his back. He makes quick work of the rest of Sam’s beer. 

* * *

Mouth tingling from the bubbles, he already feels the alcohol loosening his tongue and limbs. He probably should’ve taken Cas up on his offer to fill his stomach with solid food, but too late now. He turns to Cas, sitting in Sam’s empty seat at the other end of the couch. “Alright, lay it on me.”

Cas jumps like Dean electrocuted him instead of asking a simple not-question. Eyes wide, he turns to Dean.

“What?” Dean asks defensively. “You said you wanted to talk after. It’s after.”

“Yes, but…” Cas drifts off, swallowing, “maybe in the morning would be better.”

“You’ve been angsting about this for the past nine hours,” Dean says. “I bet you’d feel better if you got it off your chest.”

Cas’s shoulders slump. “Yes, you’re probably right,” he acknowledges, and Dean grins. “I have a proposition for you.”

“Sounds kinky.”

_“Dean.”_

“Fine,” Dean holds his hands up in the air, “go on.”

Cas clutches his beer so tightly, Dean’s a little afraid he’s going to shatter it. “I would like to offer you a job.”

Dean almost drops his own bottle. _“What?”_

Cas licks his lips. “I spoke to Naomi about a work-release program. You would be an official informant in our White Collar Crime Division. You wouldn’t be paid, of course, but you would be given a stipend for lodgings and meals. Our supervisors would expect seven to ten years, depending on how useful you turn out to be.” The corners of Cas’s mouth lift up in a small smile. “I would anticipate sooner.”

“I wouldn’t have to serve time,” Dean marvels.

Cas’s whole body relaxes as he takes in Dean’s reaction. “Not unless you violate the terms of the work-release.”

“And Sam?”

Cas doesn’t look surprised at Dean’s question. “We’d offer him a similar deal. You would have to be placed in separate departments within the division, of course - more to spread out your talents than because we fear you two collaborating on a return to crime - but you would have some opportunities to work together.”

Dean swallows, his throat dry despite all the beer. “Would you still be my handler?”

Cas hesitates. “Ah, no.”

Dean hides his disappointment behind another pull of his drink. He’s definitely tipsy now. “Well, that sucks.”

Cas's eyes widen. He sits up a little straighter, asking carefully, “Would you like it if I was your handler?”

For such a genius, Cas is such a dumbass.

Dean ignores his question. “If it’s not you, who’s it gonna be?”

“Anna or Bal, most likely.”

Dean swirls his bottle around, and he doesn’t have nearly enough alcohol left for this. “Awesome,” he mutters, “just awesome.”

Cas squints at him. “You aren’t pleased.”

“’Course I am,” Dean lies. “I got a plan now. ‘S more than I had last night.”

Cas’s expression plainly says he can see right through Dean’s bullshit. “Is there anything you’d rather do? I’m afraid you’ll have to pay some sort of debt to society.”

Dean shakes his head. “No, ‘m happy.”

With an undercurrent of frustration in his words, Cas asks sharply, “If you would rather do something else, tell me.”

“I - I thought we worked well together, alright?” Dean says, and he would slap himself for how pathetic he sounds, but he still has some self-control so his hands remain in his lap.

Cas’s head tilts as he studies Dean curiously. “After this case, Naomi said I will be promoted. I will be supervising Bal and Anna, and, I suppose, you - tangentially - if you take the job.”

Dean squashes the rising hope in his chest, and forces his face into a neutral expression. “So we’ll still work together?”

“We’ll still work together,” Cas confirms with a small smile. “Not as closely as on this case, but perhaps on other extremely high-profile incidents.”

Dean drains his beer as he struggles to come up with a response. “That’s good,” he says gruffly.

“Indeed,” Cas takes a sip of his drink, his eyes darting over to Dean every few seconds like a nervous tic.

“You’ve got something else on your mind.”

Cas freezes. “I do,” he acknowledges. He doesn’t say anything else.

“Wanna elaborate?” Dean asks almost lazily as he stretches out on the couch. He’ll get it out of Cas eventually, since apparently they have seven-to-ten years more of this thing to go.

Cas sighs, “Not especially.” He polishes off his beer and sets the empty bottle next to the others on the coffee table. He sits up straighter and turns to face Dean fully. “But I should, since we will be working together.” 

“Alright,” Dean says as he grabs the last scraps of his attention to focus on Cas, but Cas doesn’t immediately launch into whatever’s on his mind. “Not gettin’ any younger here,” he prompts.

Cas swallows forcefully. “Yes, sorry,” he says, his gaze skittering away from Dean’s face.

That’s not a good sign.

“It’s about,” Cas starts before resetting, “Well, I should begin with the fact that I kissed you earlier.”

“You can’t do that again,” Dean says before Cas can say another word. He feels painfully sober with the turn of the conversation. His mouth twists into a frown.

Cas pales. “Yes, of course,” he mumbles. “I apologize.”

“It’s fine,” Dean says even though it really isn’t. “But you can’t go fucking with my head to get me to do things, alright? I can’t get jerked around by you again - it wasn’t fun the first time, and wasn’t a fucking picnic today.”

Cas reaches out to grab Dean’s arm, like he’s afraid Dean will bolt. “I wasn’t fucking with you.”

“You sure about that?” Dean asks, eyebrows raised. Cas lets go, but Dean can still feel the warmth of Cas’s hand on his shoulder like a brand. “You used my _feelings,”_ Dean shudders at the word - he’s such a girl - but there’s no other way to say it, “to manipulate me. That’s gotta stop if you want this work-release crap to work.”

“‘Feelings?’” Cas’s eyes widen as his face goes slack. He swallows. “You have feelings for me?”

Dean makes a face. “Isn’t that what you were banking on when you pulled that shit with the bulletproof vest?”

Cas stares, saying nothing. And Dean might as well go for broke, since Cas seems to be holding all the cards. Not like that’s any different than usual.

Dean sighs. He could really use another drink now. “I - I need you, alright? I just need you in my life. I don’t care how. If it means signing onto your work-release program or visits to my cell for my birthday, I’ll take it.”

Hesitantly, like he’s afraid Dean will cut him off at any moment, Cas says, “You... reciprocate my feelings?”

Dean chokes on his own spit. _“Your_ feelings?”

Cas’s soulsearing gaze doesn’t waver. “I think I love you, Dean.” While Dean’s brain short-circuits, Cas continues, “But I wasn’t sure if you felt the same.”

“What the fuck, man?” Dean throws his hands in the air, ignores the big L word like only a Winchester can, and tells Cas, “I was the one who asked you out in the first place!”

Cas shakes his head. “I thought your feelings had changed once I told you I was part of law enforcement.”

“I mean, I wasn’t thrilled about it,” Dean says flatly. “But this shit doesn’t come with an on-off switch. And you were still _yourself_ , so - I guess it didn’t really matter.”

Cas squints at him. “You never made any indication, even when we were living together.”

“’Course I didn’t,” Dean retorts, although not strictly the truth, “I had less than a snowball’s chance. And you play things pretty close to the chest, dude.”

“I don’t think I did,” Cas says, brow furrowed. “I am not very good at lying, as you keep telling me.”

“Apparently you are, if you have a good enough reason to,” Dean says ruefully.

“I suppose,” Cas says, looking a little dazed. 

Dean gives Cas’s hand a squeeze before he tugs him closer.

Cas flails a little before he braces himself on the couch cushion with a small, “oof,” eyes a little wide as he takes in how little distance lies between them.

And then Dean leans forward to finish what Cas started in the church.

* * *

Cas refuses point-blank to have sex on his couch, so they stumble, Dean shirtless and Cas with his button-down unbuttoned, to Cas's bedroom. 

Dean lunges for the bed and twists around for Cas so they can pick up where they left off. 

But Cas is standing by the door, wringing his hands. 

Dean freezes. “Everything okay?” he asks tentatively as he hops off the bed.

Clearly conflicted, Cas nods jerkily. “Yes, of course.” He takes a step closer, a determined glint in his eye. 

“Call me crazy,” Dean says as he takes Cas’s hands in his, “but I don't think you are.”

Cas widen before he ducks his head. “I don’t - it’s not -”

“Breathe,” Dean instructs gently as he winds his arms around Cas and gives him a light squeeze. “Just tell me what you’re worried about, sweetheart, and we’ll work it out.”

Cas mumbles something into Dean’s chest.

“Didn’t catch that.”

Cas meets his gaze miserably. “It’s been a really long time, Dean.”

“That’s fine,” Dean says easily. “It’s like riding a bicycle.”

Cas looks completely devastated. “I don’t know how to ride a bicycle.”

Dean laughs. “Forget the bicycle,” he says, pressing a swift kiss to Cas’s mouth before his face can fall further. “I lied, anyway. It’s not like that since not everyone wants to be ridden the same way.” Dean smirks and tugs Cas towards the bed. “Don't worry,” he says as he catches Cas’s terrified face. “Scout’s honor, I won’t touch you unless you say so.”

“Dean…”

“What?” Dean asks as he scoots to the far end of Cas’s orgy bed.

Cas stays standing. He makes a frustrated noise in the back of his throat. “You don’t have to _baby_ me about this. We can get back to the foreplay. I’m sure I will-”

“No way,” Dean shuts him down, “You’re not gonna pressure yourself into jack shit. Nobody ever said sex was easy - well, it is if you’re an asshole who doesn’t know how to do it right.” He pats the bed next to him. “Sit down. I don’t want to talk with you looming over me.”

Cas obliges warily, still a little spooked around the eyes.

“You said it’s been a few years,” Dean says, “What are you worried about exactly? Coming too soon? Not coming soon enough?” He waggles his eyebrows. “Not knowing which position you wanna do it in first?”

Cas gulps. “What if I don’t like it?” he asks in a small voice. 

Dean shrugs. “Then we can work out more specific issues on pain or discomfort or, I don’t know, if you find lube gross or something,” he inhales a slow breath. “Or we can stop.”

“You’d do that?”

“I’ve had a lot of sex in my life,” Dean says frankly. “Sometimes my partners didn’t take the time to ask about what I liked or needed. If I had a choice between that or no sex at all, I know what I’d choose.”

“What do you want?”

“You,” Dean says shamelessly quickly.

Cas rolls his eyes. “That’s a given. What else?”

Dean lifts one shoulder in a half-shrug. “No humiliation - nothing kills my boner faster than getting called a whore or slut or any shit like that. I’m pretty open as long as you don’t spring anything on me.” He stares down at their hands. “I’d like to see you, the first time. No doggy style or reverse cowgirl.”

Cas reached out to squeeze Dean’s hand in reassurance. 

Dean raises his eyebrows. “Your turn.”

Cas nods. “That all sounds reasonable. I,” he pauses, his lips pursing. “I’m not sure, since my experience has been limited. But I also don’t want to wait to be sure.”

“I can work with that. Are you doin’ a little better?” Cas nods, so Dean says, “It doesn’t have to be perfect the first time.” He shifts on the bed, turning to face Cas properly. “Sex is a process, not an end point, got it?”

“Yes, Dean.”

Dean scoots closer, leaving precious few inches between them. “This okay?”

“Yes, Dean,” Cas says again, more impatiently this time. He untangles their hands and lays a palm on Dean’s side. He pulls him closer so they're flush together.

Cas isn’t hard yet, but he’s getting there. Dean grins and leans in for a kiss. He rests a hand on the hinge of Cas’s jaw, tilting his head so it’s not at an awkward angle or straining to stay upright. As Cas smiles against his mouth, Dean slips his tongue inside. His other hand pushes at Cas’s button down, getting it off his shoulders but stuck in his armpits.

He chuckles to himself as Cas huffs, frustrated, and throws his shirt to the floor. He plucks at his undershirt questioningly.

“Pants too,” Dean says as they stare at one another. “I’ll go first.”

Completely bare, Dean reaches for Cas again, moving their bodies so Cas is half on top of him. He recaptures Cas’s mouth with his, as his hands reach down to grip Cas’s ass.

Cas wiggles a little, adjusting himself, and most of the blood in Dean’s brain, previously keeping back his neanderthal thoughts, rushes south to his dick.

His hips jerk up, mostly involuntarily, and Cas lets out a hoarse yelp.

Dean freezes. “Okay?”

Cas nods. “Took me by surprise.” He licks his lips and deliberately grinds his pelvis down against Dean’s.

Dean lets out a groan as his fingers flex, digging into Cas’s ass. “Careful,” he murmurs against Cas’s mouth. “Don’t start anything you can’t finish.”

Cas slips his leg between Dean and tries an experimental rut, cocks sliding against each other. 

Dean lets out a moan. Cas bucks his hips again.

“Okay, okay, not the padawan I thought you were,” Dean says as he puts a hand on Cas’s chest, pressing for a flimsy extra inch of space.

“I’m not a virgin, Dean,” Cas says, his voice sinfully low.

“Clearly,” Dean grunts. “But what’re you into?”

Cas just stares at him as Dean’s familiar question falls on deaf ears.

“Top or bottom,” Dean clarifies, resigned. Cas can’t make anything easy, can he. 

Cas swallows. “I’ve done both.”

Dean presses a swift kiss to Cas’s cheek. “Why don’t you top this time? If you want to go that far, that is.”

“What do you prefer?” Cas asks curiously.

“Either works with me,” Dean says.

“Truly?”

“Yeah,” Dean says with a smile. “I wouldn’t lie to you about that, Cas. It would probably come back to bite me in the ass, anyway.”

“I don’t like pain play,” Cas says primly.

Dean laughs. “Alright, I’ll put a nix on the biting. But I’m good with whatever you want. I figure topping might be easier for you if it’s been a while. We can work up to something else if it’s not your thing.”

Cas nods. “That is acceptable.”

“Acceptable, is it?” Dean growls as he hooks his ankle around Cas’s and flips them over. He almost takes an elbow to the face in Cas’s flailing, but his dastardly good-looking face will live to see another day. He swoops down, hands roving all over Cas’s body to translate his reactions like a braille reader. A gasp as Dean idly tweaks a nipple. A groan as he sucks at the pulse point on Cas’s jaw, stubble rasping against his forehead. A full body shudder as Dean grinds their cocks together, now slippery with precome.

He pauses. “Are you clean?” he asks. “If not, we’re gonna have to get a condom on you ASAP.”

Cas rolls his eyes. “It’s been a few years, but last time I checked I was clean.”

“Good,” Dean murmurs, holding Cas flush against him as he arches his spine, putting delicious pressure against Cas’s crotch. “Same here.”

Cas spasms underneath him, a low whine sounding in his throat that barely resembles Dean’s name.

Dean kisses a trail up Cas’s neck to his ear, revelling in every one of Cas’s hitched breaths. “Got lube, angel?”

“In the drawer. Condoms too.”

“Thanks,” Dean breathes, “It’s like you read my mind.”

Cas gulps, hands fisting in the sheets as Dean deliberately slides over his body to open the drawer in the nightstand. 

Dean grabs the tube after a little blind searching and sits back on his haunches, straddling Cas’s thighs. 

“Look at you,” Dean whistles as he lets the lube fall to the bed and stares down at Cas. “All spread out for me.”

Cas squirms away under the praise, but there’s nowhere to hide.

Dean falls forward so his arms bracket Cas’s face. “You do know you’re fucking hot, right?” he purrs, “Wasn’t like I was trying to keep it a secret, jerking off in the next room over almost every night after spending hours with you, so close on the couch.”

Cas huffs. “I’m already a done deal, Dean. You don’t have to stroke my ego.” He licks his lips nervously and adds, “Just my dick.”

Dean snorts a laugh. “That was terrible. Like, Penthouse Forum bad. I love it.” He ducks down for a kiss. “And I’m not stroking your ego to get into your pants. I’m making up for lost time.”

“Lost time?” Cas tilts his head.

“Yeah,” Dean shifts his weight to one hand as he uses the other to run through Cas’s perpetual bedhead. Fuck, his hair is soft. He can’t wait to sit on that couch, with Cas’s head in his lap, as the little shit plows through Jeopardy! questions and shows Dean up on every category except pop culture. “I would’ve been telling you how many boners you gave me for months if I didn’t think you’d shoot me first.”

“I wouldn’t have shot you,” Cas says, appalled.

Dean grins. “I know that _now_.”

Cas still looks troubled, so Dean bends down for another kiss. “We’re getting off track,” he breathes against Cas’s lips. “Point is, you’re hot, and you’re gonna fuck until me until I can’t walk tomorrow. Got it?”

“Got it,” Cas nods along breathlessly.

“Good.” Dean sucks a trail of bruising kisses back down the other side of Cas’s neck, down his chest, as Cas’s ragged breaths fill the air between them. Dean tugs lightly on a nipple with his teeth, laving away the pinch with a few broad strokes of his tongue.

He raises his head, his chin brushing against Cas’s stomach. “This okay?”

Cas gulps. “Yes,” he rasps, barely audible. “I - yes.”

Dean grins as he resumes the business at hand. He presses a kiss right above Cas’s belly button as he lifts Cas’s hardened cock - Cas sucks in a breath, hips twitching - out of the way. “Dean,” Cas starts, low and wrecked.

But Dean ignores him as he laps up the little spot of bitter precome on Cas’s abdomen. Cas shivers. He tries to sit up, but Dean stops him, reaching up to splay a hand on Cas’s chest. “Do you not want me to suck you off?” he asks.

“Yes, but,” Cas breaks off, his face glowing red. “I feel… inadequate. I’m not doing any-”

“You’re letting me take care of you,” Dean says as he balances himself on his heels. “That’s not nothing.”

“But you’re-”

“Enjoying myself,” Dean finishes for him as he idly swipes his thumb over the head, smearing precome. “Trust me. Getting to hear you, watch you, as you come apart under my hands and mouth - that’s all part of the build for me.”

Cas doesn’t seem completely on board as he settles back down. He does get a little dazed look in his eye as Dean bends down. But it turns to frustration as Dean only kisses around the base of his cock.

“Dean,” Cas rumbles.

Dean looks up. “You got something to say?”

Cas frowns, mouth opening.

Dean licks a wet stripe up Cas’s cock and whatever Cas was going to say is cut off with a strangled moan. When he closes his lips around the head, Cas gives an aborted thrust up, almost choking him.

“Careful,” Dean splutters as he pulls off.

“I’m sorry,” Cas says, mortified.

“It’s okay. I wound you up pretty tight, huh.” He grins wickedly as he takes Cas back in hand. “Then we’ll have to keep going until you get used to it.”

“I don’t think I’ll ever get used to - _Dean!”_

Dean swirls his tongue around the head of Cas’s cock before swallowing him down again.

“Dean,” Cas grinds out, his body taut enough to shatter.

Dean wraps his hand around what his mouth can’t reach. He gives him a few experimental pumps now Cas is good and wet.

“I’m going to come soon,” Cas says through gritted teeth.

Dean’s hand slows to an agonizing pace.

Breathing hard, Cas tries to buck his hips further into that wet heat, but Dean’s having none of it. He draws away entirely, ignoring Cas's wounded little whine. He asks, “Have you prepped someone before?”

“Prepped?”

Dean isn’t sure if Cas is really unfamiliar with the word or if his brain is still scrambled from the mostly-accidental edging. “For dick, Cas,” Dean says, rolling his eyes. “Prepped someone so it doesn’t hurt like a motherfucker when you shove a whole cock inside them.”

Cas shakes his head.

Dean clambers back up Cas’s body to kiss away his concern. “It’s all good,” he says as he cradles Cas’s face in his palm. “I’ll show you how.”

“Thank you, Dean.”

Dean grins as he blindly roots around the sheets for the bottle of lube by Cas’s left knee. “Don’t thank me. It’ll make everything easier in the long run if you know how to do it right.”

“Is there a wrong way to do it?” Cas sits up, watching with keen eyes as Dean squirts some lube into his palm.

“Sometimes people rush through it,” Dean says with a shrug. “And if you don’t hit the right spot every once in a while, it’s a little boring.”

“Having fingers up your ass is boring?” Cas asks, eyebrows raised.

“Not everything is stimulating down there.” Dean sits back and spreads his legs before rethinking it. “Let’s switch places,” he says. “I’ll be up against the headboard so you can see what’s going on.”

Cas complies as Dean settles in, careful not to drip too much lube on the bed. Dean reaches down and circles his hole a couple times, teasing himself. For now, he ignores his hard cock, but every brush of his inner arm against his sensitive parts sends shivers down his spine.

From what he can see between his legs, Cas’s face is the picture of concentration. As Dean pushes his first slick finger into himself, Cas licks his lips. 

“Like what you see?” he asks, a tad breathlessly.

Cas nods. “You are a very erotic individual.”

Dean snorts a laugh. “Thanks.” He breathes out hard through his nose as his finger sinks down to the knuckle. “Talk to me, man.”

Cas’s eyes widen like a deer in the headlights. “I do not have a way with words like you do.”

“That’s fine,” Dean says, and before he can overthink it, “I just like the sound of your voice.”

“You do?” 

Dean throws him a look, noting with satisfaction that he’s almost ready for another finger. “You didn’t think I was _that_ interested in bees, did you?”

“They’re fascinating animals!” Cas protests, but he’s smiling.

“Uh huh,” Dean grunts as he circles his rim, two fingers now. “I’m sure you think they’re the fucking best, but you don’t hear me goin’ on and on about my car, do you?”

Cas’s face falls. “I - was I boring you?”

“Jesus Christ,” Dean mutters as he puts the prep on pause. This is what he gets for getting sappy in the middle of sex. He sits up and tugs Cas right into Dean’s space. “You weren’t boring me,” he leans forward and kisses the frown off Cas’s face, “I’m just saying, I’m like bees because _you_ like them. I think they’re cool and all, but only because they get you so riled up.” 

Cas breaks apart too soon. He still hasn’t lost the furrow between his brows. “You can talk about your car, Dean.”

“I - what?”

“This goes both ways, then,” Cas says seriously, and, at this rate, Dean will never get Cas’s cock inside him. “I want to know about your car since she’s a very big part of your life.”

“Now?” Dean asks, resigned. 

Cas makes a face. “I thought we were going to have sex now. But maybe you could show me how she works, sometime in the future?”

“Yeah,” Dean says as he pulls Cas closer and kisses him again. “I can do that.” For fucking sure he can show Cas how the Impala runs, give him tips on basic maintenance, and then fuck him over Baby’s hood like the good Lord intended.

“Good,” Cas breathes. “I believe you were showing me how you like to be prepped?”

Dean gets back in position, but Cas’s fingers curl around his wrist as he reaches down between his legs. “Can I?” he asks, his eyes dark.

“Uh, yeah,” Dean says, dazed. He tosses Cas the bottle of lube. 

Cas gets himself all slicked up and circles Dean’s rim, exactly like Dean had done. “Another?”

Dean swallows. “Yes, please.” Cas obliges, going slow enough to make Dean grind his teeth with frustration or anticipation; he’s not sure which. “’M not gonna break. You can go faster.”

Cas looks up, surprised. “But you were going so slowly.”

“The first is always the hardest,” Dean says as he resists the urge to shove himself down.

Cas bites his lip as he adds his middle finger with none of the teasingly light touches of before. “Is this okay?”

Dean breathes, “Can you-” He holds up one hand, demonstrating the gesture for Cas to mimic.

“Oh,” Cas says, brightening, “you want me to stimulate your prostate.”

Dean slumps down on the pillows. What a dork. “Yeah, Cas,” he mutters, smiling weakly. “That’s what I want.”

Cas’s fingers start moving inside him, and his dorkiness is the last thing on Dean’s mind. He sucks in a jagged breath of anticipation as Cas gets closer to the mark.

Bullseye.

Dean’s fingers tangle in the sheets as Cas deliberately rubs against the spot that sends tingles racing down his spine. His hips move of their own accord, seeking more friction, more pressure, more of everything. “Fuck, Cas, yeah - right _oh.”_

“You need to keep still,” Case growls as Dean twists, “or I cannot keep this up.”

“Hard,” Dean grunts as Cash zeroes in on his prostate and goes to fucking town. He grits his teeth, a low whine escaping as he clenches around Cas’s fingers.

“Would it be alright if I held you down?” Cas asks. 

Dean’s eyes widen. He swallows. Nods.

Cas lays a hand on Dean’s hip, his grip firm and secure. As he thrusts his fingers in, the pads just reaching the right spot, he leans forward, adding some of his own body weight to the hand keeping Dean in place.

Dean jerks as Cas adds another finger. But the slight burn of the stretch is the last thing on his mind as Cas bends down to lick the head of Dean’s cock.

Dean’s whole body spasms in response. Christ, he’s hard enough to cut glass.

Cas sits back up, pleased as fucking punch. “Was that okay?” he asks innocently.

Dean glares. “Warn a guy, why don’t you,” he says as he holds up his thumb and forefinger an inch apart, “I was this close to coming all over your face.”

“Maybe next time,” Cas says as he slides three fingers back in.

Dean’s retort cuts off with a moan as Cas picks up speed. “You’re im-fucking-possible,” Dean groans as he tries to grind down, but Cas is already withdrawing. 

Dean does _not_ whine at the loss.

“Do you think you are ready?" Cas asks. “If you’re about to orgasm, I’d like to be inside you.”

“Fuck yeah,” Dean breathes. “C’mere.” He gently manhandles Cas into position above him. Cas’s cock hangs heavy and obscene, and Dean can’t help his Cas-level stare. He gives himself a little shake and adjusts Cas’s position. 

“Are you ready?” Cas asks, sounding a little nervous but mostly breathless.

Dean nods. “Slowly, though,” he cautions as he feels Cas brush up against his entrance. “I want to feel every inch of you.”

At a torturous pace, Cas sinks into Dean. The head of his cock feels impossibly big as it stretches him open; nothing like the measly three fingers from before. It’s not painful, but he’s hovering on that borderline.

“Can you-” Dean huffs, words failing him. “Here,” he says, shifting a little, “get me used to it? Not the whole way yet.”

Cas nods, his eyes dark and intense as he edges in, slowly but surely getting Dean accustomed to the sensation. 

“Jesus Christ,” Dean pants as Cas finally nudges in the last of the way. “You’re fucking awesome, you know that?”

Cas seems almost beyond speech. He nods and reaches up one hand to card through Dean’s hair. “You are magnificent,” he says his voice hoarse.

Dean doesn't know how to respond. “You can start moving more. I think I’m good.”

Cas nods, an expression of intense concentration on his face. He slides almost all the way out, but Dean can barely register the empty feeling before Cas pushes back in. Dean bites off a whimper. It feels _so good._

Dean hooks his legs at the small of Cas’s back, urging him in deeper. He groans as Cas just presses against his prostate - it’s nowhere near as precise or intense as his fingers, but there’s plenty of other sensations to focus on. Like the flex of Cas’s muscles under the heels of his feet; the slow slide of Cas’s cock inside him; the expression on Cas’s face, so reverent it almost makes Dean look away.

Dean’s orgasm looms like a tidal wave - a slow pressure building out at sea before it crashes home. His muscles are tense like a bowstring, and every time Cas hits his sweet spot, no matter how light, it punches the breath out of his lungs. 

Cas thrusts in particularly hard, and Dean cries out.

“Are you okay?” Cas asks, freezing at once.

Dean grins, strained. “Yeah, good - just about to come. Trying not to.”

Cas’s face twitches. “Do you want to come?”

Dean nods. “Yes, please.”

Cas reaches between them, and Dean nearly blows his load as Cas’s fingers wrap around his shaft. But then Cas starts moving inside him in time with jacking him off, and Dean loses it. He comes, back arching and toes curling.

“Fuck,” Cas swears in a low voice, his mouth open. “You feel - I don’t think I can last much longer.”

“Go ahead,” Dean says dazedly, riding that post-orgasm high. He lets his legs drop back to the bed.

Cas grips Dean’s upper arms as leverage as he pistons in and out, harder than before. Dean just lies there and takes it. He’s a little oversensitive, and every brush of Cas’s chest against his spent dick makes his knees twitch.

Cas finishes inside him, his expression the picture of pure, almost agonized, ecstasy. 

“You good?” Dean asks as Cas opens his eyes.

Cas doesn’t respond with words. He leans down and presses a tender kiss to Dean’s mouth, bracing himself on one elbow as his other hand comes to cradle the side of Dean’s face. “I didn’t know it could be like that.”

Dean tries to look away.

“You can’t hide from me Dean, not like this.”

Dean bats his hand away. “Come on.” He clenches down on Cas, which is petty as fuck but might do the trick.

It does not.

Cas’s eyes do roll back in his head a little from the overstimulation, but he gets back on track before Dean can say another word. “I love you,” Cas says. “You are magnificent and insufferable, and I love every lie you’ve told me and every truth you’ve shown me. I love _you._ ”

Dean’s next words catch in his throat, but he forces them out anyway. “I love you too, Cas.”


	10. Epilogue: The Beginning

**Summary for the Chapter:**

> To Castiel’s surprise, he finds out about a year into dating that Dean Winchester hasn’t completely written off the prospect of marriage. If someone had forced Castiel into marriage not once, but seven times, he would have probably sworn off all human contact and moved to the countryside to start that bee farm. Family obligations be damned.

To Castiel’s surprise, he finds out about a year into dating that Dean Winchester hasn’t completely written off the prospect of marriage. If someone had forced Castiel into marriage not once, but seven times, he would have sworn off all human contact and moved to the countryside to start that bee farm. Family obligations be damned.

So the issue isn’t that Dean is opposed to marriage. 

The issue is that he won’t ever ask Cas to marry him. 

Cas suspects Dean’s unwillingness stems from bad memories of asking his marks the big question and a lingering doubt that he doesn’t deserve Cas, which is absolutely ridiculous and patently false. Cas has tried his best to convey this to Dean in words and actions, but Dean is, as he would tell anyone who asks, a stubborn son of a bitch.

They have that in common.

Over the next few years, Castiel pieces together Dean’s sordid proposal history.

  1. Lydia: Dean proposed to her during a romantic walk on her family’s estate at sunset. When they concluded their walk, Lydia found her entire family and a photographer waiting inside the manor to surprise her.  
  

  2. Cassie: Dean proposed to her in secret, and they eloped six days later because her family didn’t approve.  
  

  3. Bela: Dean proposed to her after whirlwind getaway spanning two continents and five countries. He bought the ring from a prestigious jeweler in Geneva and popped the question on the flight back to the States. Dean said the experience put him off planes forever - not that he had thought highly of them before.  
  

  4. Lisa: Dean proposed to her by conspicuously asking Ben for his permission while Lisa was in the next room over. He officially asked her to marry him over their next family dinner.  
  

  5. Aaron: Dean proposed to him from a jail cell after punching a white supremacist in the face at a protest.  
  

  6. Pam: Dean proposed to her after sex and Chinese takeout in her apartment.  
  

  7. Cole: Dean proposed to him in the middle of their 4th of July barbeque with all his family and friends in attendance.



The day Dean’s work-release program officially ends, Cas resolves to ask Dean to marry him. He watches Dean across the room, laughing at something Anna said while shaking the condensation from his plastic glass of champagne onto Bal's pants. Anna meets Cas's eyes over Dean's shoulder, and Dean turns, a smile lighting up his face. "Look who finally crawled out from under his pile of paperwork!"

Cas calls Sam for his permission the next weekend. He debates whether or not to get a ring for the next two weeks.

He can plan a budget in his sleep, a sting with relative ease, and a birthday party under extreme duress (with Gabriel’s help). But a proposal? Cas doesn’t know where to start.

Two months later, Cas is at his wits’ end. At least he doesn't see Dean as often at work since his new position as an expert consultant means multiple divisions regularly call on him.

“Just ask him,” Sam says, his exasperation clear over the phone. “He’ll say ‘yes’ no matter how you do it.”

“But-”

“No buts,” Sam interrupts. “You know he will.”

“It’s not that,” Cas says, impatient. “I just don’t know how.”

Sam snorts. “It can’t be that hard if Dean managed it eight times.”

“That’s exactly it,” Cas insists, “He’s done it so many times. I don’t know how to make it special.”

“You’ll make it special by doing the asking,” Sam says incredulously. “He’s never _been_ asked before, you know that, right?”

Cas blinks.

Sam laughs into the stunned silence.

Cas gets up early to drive to Hallowed Grounds and a deli on Saturday morning. With the foolproof incentive of coffee, Cas persuades Dean out of bed and into casual clothing. 

Dean glances bemusedly at the cup’s logo, but doesn’t say anything.

Once Dean is sufficiently caffeinated, Cas says, “Let’s get out of the city.”

“We visited Sam in Palo Alto last weekend,” Dean points out even as he grabs the Impala’s keys.

“Not that far,” Cas assures him. “It’s been a while since we visited the park.”

“Alright, Bear Grylls,” Dean says gamely as he opens the door, “let’s get our nature on.”

In the Impala, Dean cranks up the radio as Cas drums his fingers against the dash along to the music. He tries not to show his nerves, but Dean keeps giving him knowing looks every time they slow with traffic. 

Cas has always been terrible at keeping secrets, as Dean lovingly points out at every opportunity he can. When Dean parks next to a picnic area, Cas grabs the sunscreen in the Impala’s glove compartment, the bag containing deli breakfast sandwiches, and the frayed remains of his courage.

They pick a table partially obscured by the shade of a large oak tree to sit and eat.

Cas hands over the sunscreen and keeps breakfast hostage until Dean protects himself from melanoma. Under Cas’s watchful eye, he squirts a decent amount into his palm and starts on his arms and his face before making grabby motions for the food.

Cas smiles. “You still have sunscreen-” He leans over and rubs in the white streaks along Dean’s hairline and around his eyes. Gently, he smooths his fingers along Dean’s freckled cheeks, slides his thumb down the slope of his nose.

Dean ducks out of the way of Cas’s hands, grumbling, “Alright, you’ve had your fun.”

“I can’t help it if you are extremely good looking,” Cas says.

Dean makes a scoffing noise in his throat but doesn’t refute Cas’s words. He upturns the bag. Paper napkins, a bottle of water, and the bundled sandwiches tumble out. Without waiting for Cas to finish, Dean dives into his sandwich. “Fuck yes,” he groans as he surfaces. “Man, nothing beats breakfast.”

Cas bites his lip as he reaches for his own meal. Now he’s sitting here, with Dean, facing down the barrel of the gun, his brain is horrifyingly blank. He hardly listens as Dean extols all sorts of breakfast foods.

How does one bring up asking for someone else’s hand in marriage? 

If Cas had a ring, he could get down on one knee - clearly conveying his intent with an action. But no, he has to bring it up in conversation - and that’s far more Dean’s territory than his own.

But if Cas has learned anything since meeting Dean, risks with a trusted partner always pay off.

“Marry me.”

Dean chokes on his sandwich.

Cas probably should have led with more of a segue - or any segue at all. 

Dean thumps his chest a couple of times with his fist. Eyes watering, he meets Cas’s anxious gaze. “Wanna repeat that?” he asks, his tone carefully level. “Not sure I heard right.”

Cas swallows and reaches for the water. He can do this. Dean had told him, years ago, nerves were completely normal, even for a surefire mark - not that Dean will be his mark ever again. So Cas stands his ground: “I would like to spend the rest of my life with you, Dean Winchester. Will you marry me?”

Dean blinks at him, a bit of fried egg dangling unattractively out the corner of his mouth. He rubs at his chin with the back of his hand, and the egg falls to the table.

Cas inhales a shaky breath and waits.

Dean sets down his sandwich. “You want to marry me?” he asks seriously.

“Are you hard of hearing?” Cas can’t help but snap. “I won’t - well, I would if you asked, but I’d prefer not to - repeat myself a third time.”

Dean smiles, but it doesn’t meet his eyes. “Just makin’ sure,” he says in a faux-casual voice as he studies Cas’s face, searching for some sign.

As Dean says nothing, Cas’s nerves skyrocket.

Maybe Dean isn’t as guaranteed after all. Maybe - oh god, what if Dean had said he wouldn’t propose again because he had no intentions of marrying him? Dean could very well have been telling the truth about his views on marriage, while the entire time never intending to marry _Castiel_ in particular.

He’d thought they worked well together, both in the office and out. Dean brought Cas out of his shell. He gently prodded him with jokes he didn’t understand and tempted him with promises of sexual favors. And when Cas inevitably stuck his foot in his mouth, Dean found it hilarious but never laughed at him. Dean was his firmest pillar of support; he’d sooner blow Cas in the coat closet of Novak Manor than stay quiet when Michael said nobody had truly expected Cas’s most recent promotion.

Cas, in turn, reined in Dean’s more outlandish tendencies and showed him how to work within a system, maintain a consistent schedule, and not go insane after working the same job for more than six months.

Over the past five years, Dean never strayed. Never indicated he wanted anyone else but Cas. But Cas had read things incorrectly before - for months, even, after they first met.

Dean’s voice breaks through Cas’s spiralling thoughts. “It’s a big step.” 

“Out of the two of us,” Cas says sourly, “I believe you are the expert.”

Dean runs a hand down his face, and Cas’s heart sinks.

“Cas-”

“If you do not want to marry me,” Cas says, fighting to keep his voice level, “You do not have to convince me. A simple ‘no’ will suffice.”

“I’m not saying no.”

Cas’s gaze rakes up and down Dean’s face, but he can’t find a single lie anywhere. “You’re not?”

“’Course not,” Dean says, looking almost offended. “I’m not fuckin’ nuts.”

“But you didn’t say yes.”

“I was waiting for you to take it back,” Dean says defensively.

“Why would I take it back?” Cas demands. “It’s all I’ve thought about for months.”

Dean’s face goes slack. “Months?” he repeats.

“Two, if you want to be technical about it.” Cas squints over at Dean. “You must have realized something was up this morning. You saw the coffee. You knew these aren’t our typical weekend plans.” He gestures to the deserted picnic area.

Dean goes pink. “Yeah, I did.”

“And you’ve been through this, as we’ve discussed, eight times now.”

“Yeah, but-”

“What did you possibly think I was leading up to?” Cas asks, exasperated.

“I could tell you were buttering me up for something,” Dean says, by now the color of his favorite cherry pie, “I just thought…”

“Thought what?”

“I don’t know,” Dean throws his hands up the air, “that you wanted to have sex in the woods or something! You get weird about sex, dude.” His eyes widen. “Not in a bad way, though!”

Cas’s mouth falls open. “You thought I would do this for... _sex?”_

Dean grimaces. “Not when you say it like that, I don’t.”

“Dean, you are infuriating.”

Dean throws him a teasing grin. “But you want to marry me anyway.” Still, his words carry the slightest waver of uncertainty.

Cas dips his head. “I do.”

Dean inhales a deep breath. “Alright, Cas, since you asked so nicely,” he says as Cas snorts, “Yes, I will marry you.”

Heart full to bursting, Cas walks around the picnic table to sit next to Dean. With almost reverent hands, Cas reaches for him. 

Dean doesn’t immediately respond. Instead, a cocky grin spreads over his face. “Hell, I’ll even throw in a prenup for-”

With a growl, Cas lunges for him, and Dean cuts himself off with a loud laugh. With their lips barely an inch apart, Cas breathes, “You can be a smartass, or we can have sex in the woods to celebrate getting engaged. Your choice.”

And when presented like that, there’s really no choice at all.

**Notes for the Chapter:**

> Thank you so much for reading! I wrote this story over the past year and change, so I'm thrilled to finally be able to post it. If you have any comments to share, I'd love to hear them! ♥
> 
> I'm on Tumblr as [goldenraeofsun](https://goldenraeofsun.tumblr.com) if you'd like to follow for drabbles and updates on writing.


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